# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_A1XB1
_database_code_depnum_ccdc_archive 'CCDC 1505712'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2016-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Mp-p1B-H5 F5-I-benzene, [1,2,3]Triazolo[1,5-a]quinoline
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C6 F5 I) (C10 H7 N3)
;
_chemical_formula_sum            'C16 H7 F5 I N3'
_chemical_formula_weight         463.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.8304(9)
_cell_length_b                   15.1834(18)
_cell_length_c                   12.9152(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.176(5)
_cell_angle_gamma                90.00
_cell_volume                     1495.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      32.58

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.058
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    2.203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4882
_exptl_absorpt_correction_T_max  0.7779
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17912
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         32.62
_reflns_number_total             5100
_reflns_number_gt                4248
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0300P)²+0.4500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5100
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0651
_refine_ls_wR_factor_gt          0.0604
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.0968(2) 0.51597(10) 0.27291(12) 0.0206(3) Uani 1 1 d . . .
N12 N 0.1414(2) 0.60279(10) 0.28518(13) 0.0252(3) Uani 1 1 d . . .
N13 N 0.3104(2) 0.60430(11) 0.32778(14) 0.0284(4) Uani 1 1 d . . .
C14 C 0.3740(3) 0.52155(13) 0.34277(16) 0.0279(4) Uani 1 1 d . . .
H14 H 0.4926 0.5062 0.3726 0.033 Uiso 1 1 calc R . .
C15 C 0.2385(2) 0.46258(12) 0.30764(14) 0.0219(3) Uani 1 1 d . . .
C16 C 0.2166(3) 0.36939(13) 0.30065(14) 0.0244(4) Uani 1 1 d . . .
H16 H 0.3142 0.3313 0.3233 0.029 Uiso 1 1 calc R . .
C17 C 0.0552(3) 0.33633(12) 0.26133(14) 0.0225(4) Uani 1 1 d . . .
H17 H 0.0394 0.2743 0.2577 0.027 Uiso 1 1 calc R . .
C18 C -0.0930(2) 0.39253(12) 0.22492(14) 0.0210(3) Uani 1 1 d . . .
C19 C -0.2614(3) 0.35987(13) 0.18210(15) 0.0250(4) Uani 1 1 d . . .
H19 H -0.2801 0.2980 0.1782 0.030 Uiso 1 1 calc R . .
C20 C -0.4003(3) 0.41583(14) 0.14562(16) 0.0300(4) Uani 1 1 d . . .
H20 H -0.5138 0.3925 0.1169 0.036 Uiso 1 1 calc R . .
C21 C -0.3746(3) 0.50678(15) 0.15078(17) 0.0321(4) Uani 1 1 d . . .
H21 H -0.4709 0.5450 0.1246 0.039 Uiso 1 1 calc R . .
C22 C -0.2116(3) 0.54200(13) 0.19327(16) 0.0259(4) Uani 1 1 d . . .
H22 H -0.1947 0.6040 0.1975 0.031 Uiso 1 1 calc R . .
C23 C -0.0725(2) 0.48468(12) 0.22980(14) 0.0213(3) Uani 1 1 d . . .
C31 C 0.9199(2) 0.73355(12) 0.47752(14) 0.0215(3) Uani 1 1 d . . .
I1 I 0.662746(16) 0.697471(8) 0.409595(10) 0.02504(5) Uani 1 1 d . . .
C32 C 0.9688(3) 0.82068(12) 0.49750(15) 0.0213(3) Uani 1 1 d . . .
F32 F 0.85086(15) 0.88523(7) 0.47073(9) 0.0277(2) Uani 1 1 d . . .
C33 C 1.1384(3) 0.84359(12) 0.54435(14) 0.0224(4) Uani 1 1 d . . .
F33 F 1.18375(16) 0.92799(7) 0.56133(9) 0.0295(3) Uani 1 1 d . . .
C34 C 1.2639(3) 0.77854(13) 0.57195(15) 0.0238(4) Uani 1 1 d . . .
F34 F 1.42942(17) 0.79967(7) 0.61741(11) 0.0324(3) Uani 1 1 d . . .
C35 C 1.2181(3) 0.69147(12) 0.55218(15) 0.0231(4) Uani 1 1 d . . .
F35 F 1.34051(15) 0.62891(8) 0.57950(9) 0.0315(3) Uani 1 1 d . . .
C36 C 1.0483(3) 0.66979(12) 0.50579(15) 0.0220(3) Uani 1 1 d . . .
F36 F 1.00757(17) 0.58463(7) 0.49011(10) 0.0299(3) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 N12 1.364(2) . ?
N11 C15 1.365(2) . ?
N11 C23 1.399(2) . ?
N12 N13 1.312(2) . ?
N13 C14 1.349(3) . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.426(3) . ?
C16 C17 1.347(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.431(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.399(3) . ?
C18 C23 1.408(3) . ?
C19 C20 1.376(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.395(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.391(3) . ?
C22 H22 0.9500 . ?
C31 C36 1.383(3) . ?
C31 C32 1.385(2) . ?
C31 I1 2.0785(19) . ?
C32 F32 1.337(2) . ?
C32 C33 1.373(3) . ?
C33 F33 1.335(2) . ?
C33 C34 1.382(3) . ?
C34 F34 1.334(2) . ?
C34 C35 1.378(3) . ?
C35 F35 1.338(2) . ?
C35 C36 1.368(3) . ?
C36 F36 1.336(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N12 N11 C15 111.61(15) . . ?
N12 N11 C23 124.70(16) . . ?
C15 N11 C23 123.68(16) . . ?
N13 N12 N11 105.84(15) . . ?
N12 N13 C14 110.35(17) . . ?
N13 C14 C15 108.98(18) . . ?
N13 C14 H14 125.5 . . ?
C15 C14 H14 125.5 . . ?
N11 C15 C14 103.21(16) . . ?
N11 C15 C16 119.47(17) . . ?
C14 C15 C16 137.32(18) . . ?
C17 C16 C15 118.84(18) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 121.52(18) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C19 C18 C23 117.23(17) . . ?
C19 C18 C17 122.62(17) . . ?
C23 C18 C17 120.14(17) . . ?
C20 C19 C18 121.11(18) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C21 120.05(19) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 120.94(19) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C23 118.39(18) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 H22 120.8 . . ?
C22 C23 N11 121.38(17) . . ?
C22 C23 C18 122.28(17) . . ?
N11 C23 C18 116.34(16) . . ?
C36 C31 C32 117.79(18) . . ?
C36 C31 I1 120.19(14) . . ?
C32 C31 I1 122.02(14) . . ?
F32 C32 C33 118.04(16) . . ?
F32 C32 C31 120.47(17) . . ?
C33 C32 C31 121.49(17) . . ?
F33 C33 C32 120.67(17) . . ?
F33 C33 C34 119.82(17) . . ?
C32 C33 C34 119.50(17) . . ?
F34 C34 C35 119.86(18) . . ?
F34 C34 C33 120.27(17) . . ?
C35 C34 C33 119.87(18) . . ?
F35 C35 C36 120.71(17) . . ?
F35 C35 C34 119.42(18) . . ?
C36 C35 C34 119.87(17) . . ?
F36 C36 C35 118.29(17) . . ?
F36 C36 C31 120.21(17) . . ?
C35 C36 C31 121.48(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 N12 N13 -0.2(2) . . . . ?
C23 N11 N12 N13 -179.95(16) . . . . ?
N11 N12 N13 C14 0.0(2) . . . . ?
N12 N13 C14 C15 0.1(2) . . . . ?
N12 N11 C15 C14 0.3(2) . . . . ?
C23 N11 C15 C14 -179.98(16) . . . . ?
N12 N11 C15 C16 -179.80(16) . . . . ?
C23 N11 C15 C16 -0.1(3) . . . . ?
N13 C14 C15 N11 -0.2(2) . . . . ?
N13 C14 C15 C16 179.9(2) . . . . ?
N11 C15 C16 C17 -1.1(3) . . . . ?
C14 C15 C16 C17 178.8(2) . . . . ?
C15 C16 C17 C18 1.2(3) . . . . ?
C16 C17 C18 C19 178.88(18) . . . . ?
C16 C17 C18 C23 -0.1(3) . . . . ?
C23 C18 C19 C20 0.5(3) . . . . ?
C17 C18 C19 C20 -178.52(18) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C19 C20 C21 C22 -0.8(3) . . . . ?
C20 C21 C22 C23 0.8(3) . . . . ?
C21 C22 C23 N11 179.37(18) . . . . ?
C21 C22 C23 C18 -0.2(3) . . . . ?
N12 N11 C23 C22 1.2(3) . . . . ?
C15 N11 C23 C22 -178.48(17) . . . . ?
N12 N11 C23 C18 -179.21(16) . . . . ?
C15 N11 C23 C18 1.1(2) . . . . ?
C19 C18 C23 C22 -0.5(3) . . . . ?
C17 C18 C23 C22 178.56(17) . . . . ?
C19 C18 C23 N11 179.96(16) . . . . ?
C17 C18 C23 N11 -1.0(2) . . . . ?
C36 C31 C32 F32 179.19(16) . . . . ?
I1 C31 C32 F32 -1.8(2) . . . . ?
C36 C31 C32 C33 -0.4(3) . . . . ?
I1 C31 C32 C33 178.68(14) . . . . ?
F32 C32 C33 F33 -0.7(3) . . . . ?
C31 C32 C33 F33 178.83(16) . . . . ?
F32 C32 C33 C34 -179.31(16) . . . . ?
C31 C32 C33 C34 0.3(3) . . . . ?
F33 C33 C34 F34 1.3(3) . . . . ?
C32 C33 C34 F34 179.91(18) . . . . ?
F33 C33 C34 C35 -178.49(17) . . . . ?
C32 C33 C34 C35 0.1(3) . . . . ?
F34 C34 C35 F35 0.4(3) . . . . ?
C33 C34 C35 F35 -179.80(16) . . . . ?
F34 C34 C35 C36 179.84(18) . . . . ?
C33 C34 C35 C36 -0.3(3) . . . . ?
F35 C35 C36 F36 1.0(3) . . . . ?
C34 C35 C36 F36 -178.41(17) . . . . ?
F35 C35 C36 C31 179.68(16) . . . . ?
C34 C35 C36 C31 0.2(3) . . . . ?
C32 C31 C36 F36 178.74(16) . . . . ?
I1 C31 C36 F36 -0.3(2) . . . . ?
C32 C31 C36 C35 0.1(3) . . . . ?
I1 C31 C36 C35 -178.95(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.934
_diffrn_reflns_theta_full        31.00
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.688
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.094
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_A1XB4
_database_code_depnum_ccdc_archive 'CCDC 1505713'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2016-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Mp-p1b-Hb7 1,4-diiodotetrafluorobenzene, ([1,2,3]Triazolo[1,5-a]quinoline)2
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C6 F4 I2) (C10 H7 N3)2
;
_chemical_formula_sum            'C26 H14 F4 I2 N6'
_chemical_formula_weight         740.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6906(14)
_cell_length_b                   9.568(2)
_cell_length_c                   10.618(2)
_cell_angle_alpha                64.954(6)
_cell_angle_beta                 79.728(5)
_cell_angle_gamma                87.328(5)
_cell_volume                     605.6(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9940
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      32.87

_exptl_crystal_description       plate
_exptl_crystal_colour            bronze
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.030
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             354
_exptl_absorpt_coefficient_mu    2.657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4653
_exptl_absorpt_correction_T_max  0.7074
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15546
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         33.04
_reflns_number_total             4039
_reflns_number_gt                3909
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0200P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4039
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0188
_refine_ls_R_factor_gt           0.0181
_refine_ls_wR_factor_ref         0.0464
_refine_ls_wR_factor_gt          0.0457
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.83374(18) 0.20754(14) 0.45789(13) 0.0149(2) Uani 1 1 d . . .
N12 N 0.64021(19) 0.19922(16) 0.52325(14) 0.0198(2) Uani 1 1 d . . .
N13 N 0.6398(2) 0.26774(17) 0.60781(15) 0.0225(3) Uani 1 1 d . . .
C14 C 0.8284(2) 0.31859(19) 0.59783(16) 0.0210(3) Uani 1 1 d . . .
H14 H 0.8660 0.3712 0.6489 0.025 Uiso 1 1 calc R . .
C15 C 0.9579(2) 0.28138(17) 0.50092(15) 0.0160(2) Uani 1 1 d . . .
C16 C 1.1678(2) 0.30124(18) 0.44298(16) 0.0195(3) Uani 1 1 d . . .
H16 H 1.2569 0.3507 0.4730 0.023 Uiso 1 1 calc R . .
C17 C 1.2386(2) 0.24881(18) 0.34463(16) 0.0198(3) Uani 1 1 d . . .
H17 H 1.3787 0.2639 0.3037 0.024 Uiso 1 1 calc R . .
C18 C 1.1081(2) 0.17086(17) 0.30029(15) 0.0166(2) Uani 1 1 d . . .
C19 C 1.1803(3) 0.11175(19) 0.20101(17) 0.0245(3) Uani 1 1 d . . .
H19 H 1.3199 0.1259 0.1588 0.029 Uiso 1 1 calc R . .
C20 C 1.0514(3) 0.0335(2) 0.16414(18) 0.0296(4) Uani 1 1 d . . .
H20 H 1.1026 -0.0067 0.0973 0.035 Uiso 1 1 calc R . .
C21 C 0.8473(3) 0.01307(19) 0.22383(19) 0.0284(3) Uani 1 1 d . . .
H21 H 0.7594 -0.0402 0.1966 0.034 Uiso 1 1 calc R . .
C22 C 0.7698(3) 0.06907(18) 0.32235(17) 0.0213(3) Uani 1 1 d . . .
H22 H 0.6300 0.0541 0.3640 0.026 Uiso 1 1 calc R . .
C23 C 0.9011(2) 0.14777(16) 0.35912(14) 0.0153(2) Uani 1 1 d . . .
C31 C 0.1359(2) 0.45650(17) 0.90638(15) 0.0155(2) Uani 1 1 d . . .
I1 I 0.338314(13) 0.382714(10) 0.775792(9) 0.01712(4) Uani 1 1 d . . .
C32 C -0.0624(2) 0.40148(16) 0.95087(15) 0.0149(2) Uani 1 1 d . . .
F32 F -0.13019(14) 0.30457(11) 0.90569(10) 0.02075(18) Uani 1 1 d . . .
C36 C 0.1955(2) 0.55647(16) 0.95678(14) 0.0150(2) Uani 1 1 d . . .
F36 F 0.38531(13) 0.61559(11) 0.91718(10) 0.01989(17) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 N12 1.3442(17) . ?
N11 C15 1.3644(18) . ?
N11 C23 1.3946(18) . ?
N12 N13 1.3164(19) . ?
N13 C14 1.344(2) . ?
N13 I1 2.9379(14) . ?
C14 C15 1.379(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.415(2) . ?
C16 C17 1.346(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.430(2) . ?
C17 H17 0.9500 . ?
C18 C23 1.400(2) . ?
C18 C19 1.401(2) . ?
C19 C20 1.373(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.384(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.380(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(2) . ?
C22 H22 0.9500 . ?
C31 C32 1.376(2) . ?
C31 C36 1.3803(19) . ?
C31 I1 2.0795(13) . ?
C32 F32 1.3375(15) . ?
C32 C36 1.3802(18) 2_567 ?
C36 F36 1.3360(16) . ?
C36 C32 1.3802(18) 2_567 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N12 N11 C15 111.46(12) . . ?
N12 N11 C23 124.71(12) . . ?
C15 N11 C23 123.83(12) . . ?
N13 N12 N11 106.07(12) . . ?
N12 N13 C14 110.39(12) . . ?
N12 N13 I1 137.60(10) . . ?
C14 N13 I1 111.11(10) . . ?
N13 C14 C15 108.38(13) . . ?
N13 C14 H14 125.8 . . ?
C15 C14 H14 125.8 . . ?
N11 C15 C14 103.69(12) . . ?
N11 C15 C16 119.44(13) . . ?
C14 C15 C16 136.87(14) . . ?
C17 C16 C15 118.78(13) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 121.58(13) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C23 C18 C19 117.57(14) . . ?
C23 C18 C17 120.07(13) . . ?
C19 C18 C17 122.34(14) . . ?
C20 C19 C18 120.67(16) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 120.39(15) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 120.86(16) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C23 118.40(15) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 H22 120.8 . . ?
C22 C23 N11 121.62(13) . . ?
C22 C23 C18 122.11(13) . . ?
N11 C23 C18 116.27(12) . . ?
C32 C31 C36 117.25(12) . . ?
C32 C31 I1 120.68(10) . . ?
C36 C31 I1 122.01(10) . . ?
C31 I1 N13 175.98(5) . . ?
F32 C32 C31 120.30(12) . . ?
F32 C32 C36 118.46(12) . 2_567 ?
C31 C32 C36 121.23(12) . 2_567 ?
F36 C36 C32 117.90(12) . 2_567 ?
F36 C36 C31 120.58(12) . . ?
C32 C36 C31 121.52(13) 2_567 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 N12 N13 0.13(17) . . . . ?
C23 N11 N12 N13 179.73(13) . . . . ?
N11 N12 N13 C14 -0.22(18) . . . . ?
N11 N12 N13 I1 167.41(11) . . . . ?
N12 N13 C14 C15 0.24(19) . . . . ?
I1 N13 C14 C15 -170.86(10) . . . . ?
N12 N11 C15 C14 0.02(17) . . . . ?
C23 N11 C15 C14 -179.59(14) . . . . ?
N12 N11 C15 C16 -179.88(13) . . . . ?
C23 N11 C15 C16 0.5(2) . . . . ?
N13 C14 C15 N11 -0.15(17) . . . . ?
N13 C14 C15 C16 179.72(18) . . . . ?
N11 C15 C16 C17 1.2(2) . . . . ?
C14 C15 C16 C17 -178.69(18) . . . . ?
C15 C16 C17 C18 -1.5(2) . . . . ?
C16 C17 C18 C23 0.2(2) . . . . ?
C16 C17 C18 C19 -178.17(15) . . . . ?
C23 C18 C19 C20 -0.3(2) . . . . ?
C17 C18 C19 C20 178.05(15) . . . . ?
C18 C19 C20 C21 0.6(3) . . . . ?
C19 C20 C21 C22 -0.7(3) . . . . ?
C20 C21 C22 C23 0.6(2) . . . . ?
C21 C22 C23 N11 -179.97(14) . . . . ?
C21 C22 C23 C18 -0.4(2) . . . . ?
N12 N11 C23 C22 -1.8(2) . . . . ?
C15 N11 C23 C22 177.81(14) . . . . ?
N12 N11 C23 C18 178.67(13) . . . . ?
C15 N11 C23 C18 -1.8(2) . . . . ?
C19 C18 C23 C22 0.3(2) . . . . ?
C17 C18 C23 C22 -178.16(14) . . . . ?
C19 C18 C23 N11 179.83(13) . . . . ?
C17 C18 C23 N11 1.4(2) . . . . ?
C36 C31 C32 F32 179.79(13) . . . . ?
I1 C31 C32 F32 -2.87(19) . . . . ?
C36 C31 C32 C36 -0.6(2) . . . 2_567 ?
I1 C31 C32 C36 176.69(11) . . . 2_567 ?
C32 C31 C36 F36 -179.41(13) . . . . ?
I1 C31 C36 F36 3.29(19) . . . . ?
C32 C31 C36 C32 0.6(2) . . . 2_567 ?
I1 C31 C36 C32 -176.65(11) . . . 2_567 ?

_diffrn_measured_fraction_theta_max 0.878
_diffrn_reflns_theta_full        31.00
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.426
_refine_diff_density_min         -1.022
_refine_diff_density_rms         0.122
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_A1HB6
_database_code_depnum_ccdc_archive 'CCDC 1505714'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2016-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Mp-p1b-H11 {[1,2,3]Triazolo[1,5-a]quinoline}2, HOOC-(CH2)4-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C10 H7 N3)2 (C6 H10 O4)
;
_chemical_formula_sum            'C26 H24 N6 O4'
_chemical_formula_weight         484.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.9843(6)
_cell_length_b                   25.501(2)
_cell_length_c                   6.8129(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.111(4)
_cell_angle_gamma                90.00
_cell_volume                     1153.32(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5232
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      31.84

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9584
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11766
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         32.05
_reflns_number_total             3681
_reflns_number_gt                2796
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3681
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1181
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.50408(13) 0.32391(4) 0.48722(14) 0.0184(2) Uani 1 1 d . . .
N12 N 0.31017(14) 0.33950(4) 0.42642(16) 0.0243(2) Uani 1 1 d . . .
N13 N 0.31603(15) 0.39131(4) 0.42717(17) 0.0264(2) Uani 1 1 d . . .
C14 C 0.50754(18) 0.40843(5) 0.48602(18) 0.0239(2) Uani 1 1 d . . .
H14 H 0.5488 0.4441 0.4985 0.029 Uiso 1 1 calc R . .
C15 C 0.63460(17) 0.36541(4) 0.52544(17) 0.0192(2) Uani 1 1 d . . .
C16 C 0.84501(17) 0.35576(5) 0.58296(18) 0.0231(2) Uani 1 1 d . . .
H16 H 0.9383 0.3840 0.6112 0.028 Uiso 1 1 calc R . .
C17 C 0.90974(17) 0.30574(5) 0.59663(18) 0.0239(2) Uani 1 1 d . . .
H17 H 1.0501 0.2990 0.6312 0.029 Uiso 1 1 calc R . .
C18 C 0.77226(17) 0.26224(5) 0.56039(16) 0.0212(2) Uani 1 1 d . . .
C19 C 0.8347(2) 0.20965(5) 0.57751(19) 0.0283(3) Uani 1 1 d . . .
H19 H 0.9744 0.2018 0.6149 0.034 Uiso 1 1 calc R . .
C20 C 0.6979(2) 0.16931(5) 0.54126(19) 0.0309(3) Uani 1 1 d . . .
H20 H 0.7434 0.1340 0.5525 0.037 Uiso 1 1 calc R . .
C21 C 0.4920(2) 0.18010(5) 0.48791(19) 0.0293(3) Uani 1 1 d . . .
H21 H 0.3981 0.1520 0.4635 0.035 Uiso 1 1 calc R . .
C22 C 0.42410(18) 0.23106(5) 0.47040(18) 0.0238(2) Uani 1 1 d . . .
H22 H 0.2842 0.2385 0.4351 0.029 Uiso 1 1 calc R . .
C23 C 0.56428(17) 0.27150(4) 0.50544(16) 0.0192(2) Uani 1 1 d . . .
C31 C -0.02700(17) 0.49104(5) 0.24785(17) 0.0216(2) Uani 1 1 d . . .
O31 O -0.03922(13) 0.43939(4) 0.24246(14) 0.0294(2) Uani 1 1 d . . .
H31 H 0.089(2) 0.4255(6) 0.311(2) 0.035 Uiso 1 1 d . . .
O32 O 0.12995(13) 0.51442(3) 0.32405(15) 0.0317(2) Uani 1 1 d . . .
C32 C -0.22513(17) 0.51842(4) 0.15471(19) 0.0233(2) Uani 1 1 d . . .
H32A H -0.2064 0.5456 0.0585 0.028 Uiso 1 1 calc R . .
H32B H -0.2605 0.5367 0.2669 0.028 Uiso 1 1 calc R . .
C33 C -0.40309(16) 0.48428(4) 0.03869(18) 0.0221(2) Uani 1 1 d . . .
H33A H -0.3741 0.4676 -0.0802 0.026 Uiso 1 1 calc R . .
H33B H -0.4210 0.4561 0.1313 0.026 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 N12 1.3473(13) . ?
N11 C15 1.3680(14) . ?
N11 C23 1.3951(14) . ?
N12 N13 1.3217(14) . ?
N13 C14 1.3443(16) . ?
C14 C15 1.3837(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.4198(16) . ?
C16 C17 1.3467(17) . ?
C16 H16 0.9500 . ?
C17 C18 1.4373(17) . ?
C17 H17 0.9500 . ?
C18 C23 1.4028(16) . ?
C18 C19 1.4039(16) . ?
C19 C20 1.3730(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.397(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.3758(17) . ?
C21 H21 0.9500 . ?
C22 C23 1.3905(16) . ?
C22 H22 0.9500 . ?
C31 O32 1.2136(14) . ?
C31 O31 1.3198(15) . ?
C31 C32 1.5031(15) . ?
O31 H31 0.940(16) . ?
C32 C33 1.5222(15) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C33 1.520(2) 3_465 ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N12 N11 C15 112.14(9) . . ?
N12 N11 C23 123.81(9) . . ?
C15 N11 C23 124.04(9) . . ?
N13 N12 N11 105.48(9) . . ?
N12 N13 C14 110.64(10) . . ?
N13 C14 C15 108.61(10) . . ?
N13 C14 H14 125.7 . . ?
C15 C14 H14 125.7 . . ?
N11 C15 C14 103.13(10) . . ?
N11 C15 C16 119.32(10) . . ?
C14 C15 C16 137.51(11) . . ?
C17 C16 C15 118.67(11) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C16 C17 C18 121.81(11) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C23 C18 C19 116.87(11) . . ?
C23 C18 C17 119.81(10) . . ?
C19 C18 C17 123.33(11) . . ?
C20 C19 C18 121.34(12) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 120.12(12) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 120.53(12) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 118.70(12) . . ?
C21 C22 H22 120.7 . . ?
C23 C22 H22 120.7 . . ?
C22 C23 N11 121.24(10) . . ?
C22 C23 C18 122.44(11) . . ?
N11 C23 C18 116.32(10) . . ?
O32 C31 O31 122.97(11) . . ?
O32 C31 C32 122.88(11) . . ?
O31 C31 C32 114.13(10) . . ?
C31 O31 H31 108.7(9) . . ?
C31 C32 C33 116.71(10) . . ?
C31 C32 H32A 108.1 . . ?
C33 C32 H32A 108.1 . . ?
C31 C32 H32B 108.1 . . ?
C33 C32 H32B 108.1 . . ?
H32A C32 H32B 107.3 . . ?
C33 C33 C32 111.96(12) 3_465 . ?
C33 C33 H33A 109.2 3_465 . ?
C32 C33 H33A 109.2 . . ?
C33 C33 H33B 109.2 3_465 . ?
C32 C33 H33B 109.2 . . ?
H33A C33 H33B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 N12 N13 -0.50(13) . . . . ?
C23 N11 N12 N13 -179.45(10) . . . . ?
N11 N12 N13 C14 0.16(13) . . . . ?
N12 N13 C14 C15 0.22(14) . . . . ?
N12 N11 C15 C14 0.61(13) . . . . ?
C23 N11 C15 C14 179.56(10) . . . . ?
N12 N11 C15 C16 -177.45(10) . . . . ?
C23 N11 C15 C16 1.50(16) . . . . ?
N13 C14 C15 N11 -0.49(13) . . . . ?
N13 C14 C15 C16 177.01(13) . . . . ?
N11 C15 C16 C17 0.49(17) . . . . ?
C14 C15 C16 C17 -176.72(13) . . . . ?
C15 C16 C17 C18 -1.78(17) . . . . ?
C16 C17 C18 C23 1.19(17) . . . . ?
C16 C17 C18 C19 -178.62(11) . . . . ?
C23 C18 C19 C20 0.23(17) . . . . ?
C17 C18 C19 C20 -179.95(11) . . . . ?
C18 C19 C20 C21 -0.58(18) . . . . ?
C19 C20 C21 C22 0.23(19) . . . . ?
C20 C21 C22 C23 0.44(18) . . . . ?
C21 C22 C23 N11 179.14(10) . . . . ?
C21 C22 C23 C18 -0.81(17) . . . . ?
N12 N11 C23 C22 -3.16(17) . . . . ?
C15 N11 C23 C22 178.01(10) . . . . ?
N12 N11 C23 C18 176.78(10) . . . . ?
C15 N11 C23 C18 -2.04(16) . . . . ?
C19 C18 C23 C22 0.47(17) . . . . ?
C17 C18 C23 C22 -179.36(11) . . . . ?
C19 C18 C23 N11 -179.47(10) . . . . ?
C17 C18 C23 N11 0.70(15) . . . . ?
O32 C31 C32 C33 171.70(12) . . . . ?
O31 C31 C32 C33 -9.34(15) . . . . ?
C31 C32 C33 C33 177.01(12) . . . 3_465 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O31 H31 N13 0.940(16) 1.767(16) 2.7022(13) 172.5(14) .

_diffrn_measured_fraction_theta_max 0.916
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.054
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_A1
_database_code_depnum_ccdc_archive 'CCDC 1505715'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2016-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Mp-p1b-H10 [1,2,3]Triazolo[1,5-a]quinoline
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H7 N3'
_chemical_formula_sum            'C10 H7 N3'
_chemical_formula_weight         169.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   10.9465(10)
_cell_length_b                   8.6731(8)
_cell_length_c                   50.527(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.861(4)
_cell_angle_gamma                90.00
_cell_volume                     4786.2(8)
_cell_formula_units_Z            24
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3054
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.28

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2112
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9771
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21202
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_av_sigmaI/netI    0.0909
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -68
_diffrn_reflns_limit_l_max       68
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         30.03
_reflns_number_total             6479
_reflns_number_gt                3499
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6479
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1308
_refine_ls_R_factor_gt           0.0697
_refine_ls_wR_factor_ref         0.2101
_refine_ls_wR_factor_gt          0.1808
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11_1 N 0.46307(17) 0.5322(2) 0.63742(3) 0.0320(4) Uani 1 1 d . . .
N12_1 N 0.53343(19) 0.6525(2) 0.63031(4) 0.0402(5) Uani 1 1 d . . .
N13_1 N 0.5137(2) 0.6679(3) 0.60450(4) 0.0465(5) Uani 1 1 d . . .
C14_1 C 0.4319(2) 0.5620(3) 0.59514(5) 0.0446(6) Uani 1 1 d . . .
H14_1 H 0.4023 0.5513 0.5771 0.053 Uiso 1 1 calc R . .
C15_1 C 0.3979(2) 0.4715(3) 0.61582(4) 0.0347(5) Uani 1 1 d . . .
C16_1 C 0.3173(2) 0.3451(3) 0.61978(5) 0.0373(5) Uani 1 1 d . . .
H16_1 H 0.2700 0.3013 0.6052 0.045 Uiso 1 1 calc R . .
C17_1 C 0.3094(2) 0.2890(3) 0.64450(4) 0.0345(5) Uani 1 1 d . . .
H17_1 H 0.2562 0.2047 0.6472 0.041 Uiso 1 1 calc R . .
C18_1 C 0.3794(2) 0.3538(2) 0.66698(4) 0.0314(5) Uani 1 1 d . . .
C19_1 C 0.3705(2) 0.3013(3) 0.69298(5) 0.0370(5) Uani 1 1 d . . .
H19_1 H 0.3186 0.2164 0.6961 0.044 Uiso 1 1 calc R . .
C20_1 C 0.4350(2) 0.3697(3) 0.71397(5) 0.0381(5) Uani 1 1 d . . .
H20_1 H 0.4270 0.3324 0.7314 0.046 Uiso 1 1 calc R . .
C21_1 C 0.5125(2) 0.4944(3) 0.70980(4) 0.0372(5) Uani 1 1 d . . .
H21_1 H 0.5571 0.5415 0.7244 0.045 Uiso 1 1 calc R . .
C22_1 C 0.5241(2) 0.5485(3) 0.68450(4) 0.0335(5) Uani 1 1 d . . .
H22_1 H 0.5773 0.6323 0.6815 0.040 Uiso 1 1 calc R . .
C23_1 C 0.45715(19) 0.4796(2) 0.66333(4) 0.0286(5) Uani 1 1 d . . .
N11_2 N 0.16135(17) 0.4378(2) 0.51179(4) 0.0338(4) Uani 1 1 d . . .
N12_2 N 0.21950(19) 0.5336(2) 0.52945(4) 0.0413(5) Uani 1 1 d . . .
N13_2 N 0.1938(2) 0.4848(3) 0.55321(4) 0.0468(5) Uani 1 1 d . . .
C14_2 C 0.1197(2) 0.3592(3) 0.55078(5) 0.0433(6) Uani 1 1 d . . .
H14_2 H 0.0887 0.3035 0.5651 0.052 Uiso 1 1 calc R . .
C15_2 C 0.0970(2) 0.3258(3) 0.52439(5) 0.0360(5) Uani 1 1 d . . .
C16_2 C 0.0303(2) 0.2139(3) 0.50865(5) 0.0397(6) Uani 1 1 d . . .
H16_2 H -0.0150 0.1359 0.5168 0.048 Uiso 1 1 calc R . .
C17_2 C 0.0322(2) 0.2200(3) 0.48202(5) 0.0384(6) Uani 1 1 d . . .
H17_2 H -0.0102 0.1433 0.4716 0.046 Uiso 1 1 calc R . .
C18_2 C 0.0968(2) 0.3393(2) 0.46892(5) 0.0349(5) Uani 1 1 d . . .
C19_2 C 0.0965(2) 0.3526(3) 0.44141(5) 0.0441(6) Uani 1 1 d . . .
H19_2 H 0.0547 0.2776 0.4305 0.053 Uiso 1 1 calc R . .
C20_2 C 0.1558(3) 0.4723(3) 0.42982(5) 0.0503(7) Uani 1 1 d . . .
H20_2 H 0.1545 0.4795 0.4110 0.060 Uiso 1 1 calc R . .
C21_2 C 0.2176(3) 0.5825(3) 0.44547(5) 0.0486(6) Uani 1 1 d . . .
H21_2 H 0.2575 0.6653 0.4373 0.058 Uiso 1 1 calc R . .
C22_2 C 0.2216(2) 0.5736(3) 0.47244(5) 0.0408(6) Uani 1 1 d . . .
H22_2 H 0.2644 0.6492 0.4830 0.049 Uiso 1 1 calc R . .
C23_2 C 0.1621(2) 0.4518(2) 0.48427(4) 0.0338(5) Uani 1 1 d . . .
N11_3 N 0.28864(17) 0.8242(2) 0.29645(4) 0.0331(4) Uani 1 1 d . . .
N12_3 N 0.21618(19) 0.7390(2) 0.27933(4) 0.0431(5) Uani 1 1 d . . .
N13_3 N 0.2258(2) 0.7969(2) 0.25560(4) 0.0487(6) Uani 1 1 d . . .
C14_3 C 0.3037(3) 0.9189(3) 0.25723(5) 0.0460(6) Uani 1 1 d . . .
H14_3 H 0.3257 0.9801 0.2427 0.055 Uiso 1 1 calc R . .
C15_3 C 0.3459(2) 0.9399(2) 0.28318(5) 0.0373(5) Uani 1 1 d . . .
C16_3 C 0.4221(2) 1.0437(3) 0.29812(5) 0.0422(6) Uani 1 1 d . . .
H16_3 H 0.4632 1.1238 0.2895 0.051 Uiso 1 1 calc R . .
C17_3 C 0.4364(2) 1.0287(3) 0.32467(5) 0.0401(6) Uani 1 1 d . . .
H17_3 H 0.4862 1.1005 0.3347 0.048 Uiso 1 1 calc R . .
C18_3 C 0.3776(2) 0.9057(3) 0.33828(4) 0.0355(5) Uani 1 1 d . . .
C19_3 C 0.3909(2) 0.8857(3) 0.36574(5) 0.0471(6) Uani 1 1 d . . .
H19_3 H 0.4403 0.9555 0.3763 0.056 Uiso 1 1 calc R . .
C20_3 C 0.3334(3) 0.7664(3) 0.37771(5) 0.0563(8) Uani 1 1 d . . .
H20_3 H 0.3429 0.7547 0.3964 0.068 Uiso 1 1 calc R . .
C21_3 C 0.2615(3) 0.6626(3) 0.36266(6) 0.0544(7) Uani 1 1 d . . .
H21_3 H 0.2228 0.5801 0.3712 0.065 Uiso 1 1 calc R . .
C22_3 C 0.2459(2) 0.6780(3) 0.33571(5) 0.0428(6) Uani 1 1 d . . .
H22_3 H 0.1972 0.6064 0.3254 0.051 Uiso 1 1 calc R . .
C23_3 C 0.3026(2) 0.8001(2) 0.32363(4) 0.0329(5) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11_1 N12_1 1.360(3) . ?
N11_1 C15_1 1.368(3) . ?
N11_1 C23_1 1.392(3) . ?
N12_1 N13_1 1.314(3) . ?
N13_1 C14_1 1.346(3) . ?
C14_1 C15_1 1.378(3) . ?
C14_1 H14_1 0.9500 . ?
C15_1 C16_1 1.430(3) . ?
C16_1 C17_1 1.349(3) . ?
C16_1 H16_1 0.9500 . ?
C17_1 C18_1 1.441(3) . ?
C17_1 H17_1 0.9500 . ?
C18_1 C19_1 1.400(3) . ?
C18_1 C23_1 1.404(3) . ?
C19_1 C20_1 1.369(3) . ?
C19_1 H19_1 0.9500 . ?
C20_1 C21_1 1.399(3) . ?
C20_1 H20_1 0.9500 . ?
C21_1 C22_1 1.376(3) . ?
C21_1 H21_1 0.9500 . ?
C22_1 C23_1 1.390(3) . ?
C22_1 H22_1 0.9500 . ?
N11_2 N12_2 1.348(3) . ?
N11_2 C15_2 1.381(3) . ?
N11_2 C23_2 1.396(3) . ?
N12_2 N13_2 1.321(3) . ?
N13_2 C14_2 1.359(3) . ?
C14_2 C15_2 1.371(3) . ?
C14_2 H14_2 0.9500 . ?
C15_2 C16_2 1.424(3) . ?
C16_2 C17_2 1.349(3) . ?
C16_2 H16_2 0.9500 . ?
C17_2 C18_2 1.439(3) . ?
C17_2 H17_2 0.9500 . ?
C18_2 C19_2 1.395(3) . ?
C18_2 C23_2 1.411(3) . ?
C19_2 C20_2 1.376(4) . ?
C19_2 H19_2 0.9500 . ?
C20_2 C21_2 1.387(4) . ?
C20_2 H20_2 0.9500 . ?
C21_2 C22_2 1.362(3) . ?
C21_2 H21_2 0.9500 . ?
C22_2 C23_2 1.397(3) . ?
C22_2 H22_2 0.9500 . ?
N11_3 N12_3 1.353(3) . ?
N11_3 C15_3 1.380(3) . ?
N11_3 C23_3 1.387(3) . ?
N12_3 N13_3 1.310(3) . ?
N13_3 C14_3 1.358(3) . ?
C14_3 C15_3 1.373(3) . ?
C14_3 H14_3 0.9500 . ?
C15_3 C16_3 1.411(3) . ?
C16_3 C17_3 1.346(3) . ?
C16_3 H16_3 0.9500 . ?
C17_3 C18_3 1.444(3) . ?
C17_3 H17_3 0.9500 . ?
C18_3 C19_3 1.396(3) . ?
C18_3 C23_3 1.407(3) . ?
C19_3 C20_3 1.373(4) . ?
C19_3 H19_3 0.9500 . ?
C20_3 C21_3 1.388(4) . ?
C20_3 H20_3 0.9500 . ?
C21_3 C22_3 1.367(4) . ?
C21_3 H21_3 0.9500 . ?
C22_3 C23_3 1.390(3) . ?
C22_3 H22_3 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N12_1 N11_1 C15_1 111.03(18) . . ?
N12_1 N11_1 C23_1 124.27(17) . . ?
C15_1 N11_1 C23_1 124.69(19) . . ?
N13_1 N12_1 N11_1 106.38(17) . . ?
N12_1 N13_1 C14_1 109.89(19) . . ?
N13_1 C14_1 C15_1 109.2(2) . . ?
N13_1 C14_1 H14_1 125.4 . . ?
C15_1 C14_1 H14_1 125.4 . . ?
N11_1 C15_1 C14_1 103.4(2) . . ?
N11_1 C15_1 C16_1 118.5(2) . . ?
C14_1 C15_1 C16_1 138.0(2) . . ?
C17_1 C16_1 C15_1 118.98(19) . . ?
C17_1 C16_1 H16_1 120.5 . . ?
C15_1 C16_1 H16_1 120.5 . . ?
C16_1 C17_1 C18_1 121.7(2) . . ?
C16_1 C17_1 H17_1 119.1 . . ?
C18_1 C17_1 H17_1 119.1 . . ?
C19_1 C18_1 C23_1 117.20(19) . . ?
C19_1 C18_1 C17_1 123.1(2) . . ?
C23_1 C18_1 C17_1 119.7(2) . . ?
C20_1 C19_1 C18_1 121.4(2) . . ?
C20_1 C19_1 H19_1 119.3 . . ?
C18_1 C19_1 H19_1 119.3 . . ?
C19_1 C20_1 C21_1 120.3(2) . . ?
C19_1 C20_1 H20_1 119.8 . . ?
C21_1 C20_1 H20_1 119.8 . . ?
C22_1 C21_1 C20_1 119.9(2) . . ?
C22_1 C21_1 H21_1 120.0 . . ?
C20_1 C21_1 H21_1 120.0 . . ?
C21_1 C22_1 C23_1 119.4(2) . . ?
C21_1 C22_1 H22_1 120.3 . . ?
C23_1 C22_1 H22_1 120.3 . . ?
C22_1 C23_1 N11_1 121.8(2) . . ?
C22_1 C23_1 C18_1 121.7(2) . . ?
N11_1 C23_1 C18_1 116.43(18) . . ?
N12_2 N11_2 C15_2 111.18(18) . . ?
N12_2 N11_2 C23_2 124.87(18) . . ?
C15_2 N11_2 C23_2 123.92(18) . . ?
N13_2 N12_2 N11_2 106.54(19) . . ?
N12_2 N13_2 C14_2 109.69(19) . . ?
N13_2 C14_2 C15_2 109.0(2) . . ?
N13_2 C14_2 H14_2 125.5 . . ?
C15_2 C14_2 H14_2 125.5 . . ?
C14_2 C15_2 N11_2 103.6(2) . . ?
C14_2 C15_2 C16_2 137.7(2) . . ?
N11_2 C15_2 C16_2 118.7(2) . . ?
C17_2 C16_2 C15_2 119.3(2) . . ?
C17_2 C16_2 H16_2 120.4 . . ?
C15_2 C16_2 H16_2 120.4 . . ?
C16_2 C17_2 C18_2 121.9(2) . . ?
C16_2 C17_2 H17_2 119.1 . . ?
C18_2 C17_2 H17_2 119.1 . . ?
C19_2 C18_2 C23_2 117.3(2) . . ?
C19_2 C18_2 C17_2 123.3(2) . . ?
C23_2 C18_2 C17_2 119.4(2) . . ?
C20_2 C19_2 C18_2 121.1(2) . . ?
C20_2 C19_2 H19_2 119.4 . . ?
C18_2 C19_2 H19_2 119.4 . . ?
C19_2 C20_2 C21_2 120.2(2) . . ?
C19_2 C20_2 H20_2 119.9 . . ?
C21_2 C20_2 H20_2 119.9 . . ?
C22_2 C21_2 C20_2 120.8(2) . . ?
C22_2 C21_2 H21_2 119.6 . . ?
C20_2 C21_2 H21_2 119.6 . . ?
C21_2 C22_2 C23_2 119.1(2) . . ?
C21_2 C22_2 H22_2 120.4 . . ?
C23_2 C22_2 H22_2 120.4 . . ?
N11_2 C23_2 C22_2 121.8(2) . . ?
N11_2 C23_2 C18_2 116.77(19) . . ?
C22_2 C23_2 C18_2 121.4(2) . . ?
N12_3 N11_3 C15_3 110.62(19) . . ?
N12_3 N11_3 C23_3 124.86(19) . . ?
C15_3 N11_3 C23_3 124.52(18) . . ?
N13_3 N12_3 N11_3 107.2(2) . . ?
N12_3 N13_3 C14_3 109.4(2) . . ?
N13_3 C14_3 C15_3 109.3(2) . . ?
N13_3 C14_3 H14_3 125.4 . . ?
C15_3 C14_3 H14_3 125.4 . . ?
C14_3 C15_3 N11_3 103.5(2) . . ?
C14_3 C15_3 C16_3 138.1(2) . . ?
N11_3 C15_3 C16_3 118.4(2) . . ?
C17_3 C16_3 C15_3 119.7(2) . . ?
C17_3 C16_3 H16_3 120.1 . . ?
C15_3 C16_3 H16_3 120.1 . . ?
C16_3 C17_3 C18_3 121.4(2) . . ?
C16_3 C17_3 H17_3 119.3 . . ?
C18_3 C17_3 H17_3 119.3 . . ?
C19_3 C18_3 C23_3 117.4(2) . . ?
C19_3 C18_3 C17_3 123.0(2) . . ?
C23_3 C18_3 C17_3 119.6(2) . . ?
C20_3 C19_3 C18_3 120.8(2) . . ?
C20_3 C19_3 H19_3 119.6 . . ?
C18_3 C19_3 H19_3 119.6 . . ?
C19_3 C20_3 C21_3 120.4(3) . . ?
C19_3 C20_3 H20_3 119.8 . . ?
C21_3 C20_3 H20_3 119.8 . . ?
C22_3 C21_3 C20_3 120.7(3) . . ?
C22_3 C21_3 H21_3 119.6 . . ?
C20_3 C21_3 H21_3 119.6 . . ?
C21_3 C22_3 C23_3 118.8(2) . . ?
C21_3 C22_3 H22_3 120.6 . . ?
C23_3 C22_3 H22_3 120.6 . . ?
N11_3 C23_3 C22_3 121.8(2) . . ?
N11_3 C23_3 C18_3 116.40(19) . . ?
C22_3 C23_3 C18_3 121.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15_1 N11_1 N12_1 N13_1 -0.2(3) . . . . ?
C23_1 N11_1 N12_1 N13_1 -179.4(2) . . . . ?
N11_1 N12_1 N13_1 C14_1 0.7(3) . . . . ?
N12_1 N13_1 C14_1 C15_1 -0.9(3) . . . . ?
N12_1 N11_1 C15_1 C14_1 -0.3(3) . . . . ?
C23_1 N11_1 C15_1 C14_1 178.8(2) . . . . ?
N12_1 N11_1 C15_1 C16_1 -179.0(2) . . . . ?
C23_1 N11_1 C15_1 C16_1 0.1(3) . . . . ?
N13_1 C14_1 C15_1 N11_1 0.7(3) . . . . ?
N13_1 C14_1 C15_1 C16_1 179.0(3) . . . . ?
N11_1 C15_1 C16_1 C17_1 -0.8(3) . . . . ?
C14_1 C15_1 C16_1 C17_1 -178.9(3) . . . . ?
C15_1 C16_1 C17_1 C18_1 0.4(3) . . . . ?
C16_1 C17_1 C18_1 C19_1 178.0(2) . . . . ?
C16_1 C17_1 C18_1 C23_1 0.7(3) . . . . ?
C23_1 C18_1 C19_1 C20_1 0.0(3) . . . . ?
C17_1 C18_1 C19_1 C20_1 -177.4(2) . . . . ?
C18_1 C19_1 C20_1 C21_1 -0.4(3) . . . . ?
C19_1 C20_1 C21_1 C22_1 0.0(3) . . . . ?
C20_1 C21_1 C22_1 C23_1 0.7(3) . . . . ?
C21_1 C22_1 C23_1 N11_1 178.4(2) . . . . ?
C21_1 C22_1 C23_1 C18_1 -1.2(3) . . . . ?
N12_1 N11_1 C23_1 C22_1 0.4(3) . . . . ?
C15_1 N11_1 C23_1 C22_1 -178.7(2) . . . . ?
N12_1 N11_1 C23_1 C18_1 180.0(2) . . . . ?
C15_1 N11_1 C23_1 C18_1 0.9(3) . . . . ?
C19_1 C18_1 C23_1 C22_1 0.8(3) . . . . ?
C17_1 C18_1 C23_1 C22_1 178.3(2) . . . . ?
C19_1 C18_1 C23_1 N11_1 -178.80(19) . . . . ?
C17_1 C18_1 C23_1 N11_1 -1.3(3) . . . . ?
C15_2 N11_2 N12_2 N13_2 0.2(2) . . . . ?
C23_2 N11_2 N12_2 N13_2 178.2(2) . . . . ?
N11_2 N12_2 N13_2 C14_2 -0.1(3) . . . . ?
N12_2 N13_2 C14_2 C15_2 0.1(3) . . . . ?
N13_2 C14_2 C15_2 N11_2 0.0(3) . . . . ?
N13_2 C14_2 C15_2 C16_2 179.5(3) . . . . ?
N12_2 N11_2 C15_2 C14_2 -0.1(2) . . . . ?
C23_2 N11_2 C15_2 C14_2 -178.2(2) . . . . ?
N12_2 N11_2 C15_2 C16_2 -179.73(19) . . . . ?
C23_2 N11_2 C15_2 C16_2 2.2(3) . . . . ?
C14_2 C15_2 C16_2 C17_2 -179.2(3) . . . . ?
N11_2 C15_2 C16_2 C17_2 0.3(3) . . . . ?
C15_2 C16_2 C17_2 C18_2 -1.9(3) . . . . ?
C16_2 C17_2 C18_2 C19_2 -177.3(2) . . . . ?
C16_2 C17_2 C18_2 C23_2 1.3(3) . . . . ?
C23_2 C18_2 C19_2 C20_2 -1.2(3) . . . . ?
C17_2 C18_2 C19_2 C20_2 177.4(2) . . . . ?
C18_2 C19_2 C20_2 C21_2 0.1(4) . . . . ?
C19_2 C20_2 C21_2 C22_2 0.6(4) . . . . ?
C20_2 C21_2 C22_2 C23_2 -0.3(4) . . . . ?
N12_2 N11_2 C23_2 C22_2 -2.4(3) . . . . ?
C15_2 N11_2 C23_2 C22_2 175.4(2) . . . . ?
N12_2 N11_2 C23_2 C18_2 179.4(2) . . . . ?
C15_2 N11_2 C23_2 C18_2 -2.9(3) . . . . ?
C21_2 C22_2 C23_2 N11_2 -179.0(2) . . . . ?
C21_2 C22_2 C23_2 C18_2 -0.8(4) . . . . ?
C19_2 C18_2 C23_2 N11_2 179.8(2) . . . . ?
C17_2 C18_2 C23_2 N11_2 1.1(3) . . . . ?
C19_2 C18_2 C23_2 C22_2 1.5(3) . . . . ?
C17_2 C18_2 C23_2 C22_2 -177.2(2) . . . . ?
C15_3 N11_3 N12_3 N13_3 0.1(2) . . . . ?
C23_3 N11_3 N12_3 N13_3 179.36(19) . . . . ?
N11_3 N12_3 N13_3 C14_3 0.0(3) . . . . ?
N12_3 N13_3 C14_3 C15_3 0.0(3) . . . . ?
N13_3 C14_3 C15_3 N11_3 0.1(3) . . . . ?
N13_3 C14_3 C15_3 C16_3 -177.3(3) . . . . ?
N12_3 N11_3 C15_3 C14_3 -0.1(2) . . . . ?
C23_3 N11_3 C15_3 C14_3 -179.38(19) . . . . ?
N12_3 N11_3 C15_3 C16_3 177.9(2) . . . . ?
C23_3 N11_3 C15_3 C16_3 -1.4(3) . . . . ?
C14_3 C15_3 C16_3 C17_3 176.5(3) . . . . ?
N11_3 C15_3 C16_3 C17_3 -0.6(3) . . . . ?
C15_3 C16_3 C17_3 C18_3 1.6(3) . . . . ?
C16_3 C17_3 C18_3 C19_3 179.5(2) . . . . ?
C16_3 C17_3 C18_3 C23_3 -0.7(3) . . . . ?
C23_3 C18_3 C19_3 C20_3 0.6(3) . . . . ?
C17_3 C18_3 C19_3 C20_3 -179.7(2) . . . . ?
C18_3 C19_3 C20_3 C21_3 0.4(4) . . . . ?
C19_3 C20_3 C21_3 C22_3 -0.5(4) . . . . ?
C20_3 C21_3 C22_3 C23_3 -0.5(4) . . . . ?
N12_3 N11_3 C23_3 C22_3 3.2(3) . . . . ?
C15_3 N11_3 C23_3 C22_3 -177.6(2) . . . . ?
N12_3 N11_3 C23_3 C18_3 -177.02(19) . . . . ?
C15_3 N11_3 C23_3 C18_3 2.2(3) . . . . ?
C21_3 C22_3 C23_3 N11_3 -178.7(2) . . . . ?
C21_3 C22_3 C23_3 C18_3 1.5(3) . . . . ?
C19_3 C18_3 C23_3 N11_3 178.65(19) . . . . ?
C17_3 C18_3 C23_3 N11_3 -1.1(3) . . . . ?
C19_3 C18_3 C23_3 C22_3 -1.6(3) . . . . ?
C17_3 C18_3 C23_3 C22_3 178.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.926
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.057
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_A1HB9
_database_code_depnum_ccdc_archive 'CCDC 1505716'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2016-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Mp-p1b-H21 [1,2,3]Triazolo[1,5-a]quinoline, 2-F-PhCOOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C10 H7 N3) (C7 H5 O2 F)
;
_chemical_formula_sum            'C17 H12 F N3 O2'
_chemical_formula_weight         309.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.3976(15)
_cell_length_b                   20.616(5)
_cell_length_c                   10.876(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.126(9)
_cell_angle_gamma                90.00
_cell_volume                     1420.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6487
_cell_measurement_theta_min      3.37
_cell_measurement_theta_max      31.71

_exptl_crystal_description       prism
_exptl_crystal_colour            bronze
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9566
_exptl_absorpt_correction_T_max  0.9852
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15510
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         32.62
_reflns_number_total             4619
_reflns_number_gt                3314
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4619
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1439
_refine_ls_wR_factor_gt          0.1288
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.81364(14) 0.52710(5) 0.81778(9) 0.0264(2) Uani 1 1 d . . .
N12 N 0.63165(15) 0.49324(5) 0.79436(10) 0.0313(2) Uani 1 1 d . . .
N13 N 0.63654(17) 0.46483(6) 0.68577(10) 0.0355(3) Uani 1 1 d . . .
C14 C 0.8149(2) 0.47968(7) 0.64071(12) 0.0361(3) Uani 1 1 d . . .
H14 H 0.8530 0.4648 0.5642 0.043 Uiso 1 1 calc R . .
C15 C 0.93409(18) 0.52024(6) 0.72403(11) 0.0306(3) Uani 1 1 d . . .
C16 C 1.13140(18) 0.55312(7) 0.73436(12) 0.0345(3) Uani 1 1 d . . .
H16 H 1.2179 0.5494 0.6706 0.041 Uiso 1 1 calc R . .
C17 C 1.19416(19) 0.58961(7) 0.83576(13) 0.0344(3) Uani 1 1 d . . .
H17 H 1.3252 0.6119 0.8420 0.041 Uiso 1 1 calc R . .
C18 C 1.06853(18) 0.59575(6) 0.93437(12) 0.0293(3) Uani 1 1 d . . .
C19 C 1.1323(2) 0.63220(6) 1.04270(13) 0.0360(3) Uani 1 1 d . . .
H19 H 1.2632 0.6546 1.0516 0.043 Uiso 1 1 calc R . .
C20 C 1.0084(2) 0.63586(7) 1.13564(13) 0.0389(3) Uani 1 1 d . . .
H20 H 1.0544 0.6604 1.2084 0.047 Uiso 1 1 calc R . .
C21 C 0.8149(2) 0.60362(7) 1.12326(13) 0.0368(3) Uani 1 1 d . . .
H21 H 0.7300 0.6063 1.1880 0.044 Uiso 1 1 calc R . .
C22 C 0.74500(19) 0.56787(6) 1.01826(12) 0.0306(3) Uani 1 1 d . . .
H22 H 0.6124 0.5464 1.0098 0.037 Uiso 1 1 calc R . .
C23 C 0.87230(17) 0.56393(6) 0.92522(11) 0.0258(2) Uani 1 1 d . . .
C31 C 0.21444(18) 0.32499(6) 0.39758(11) 0.0291(3) Uani 1 1 d . . .
C37 C 0.37494(19) 0.36961(6) 0.46615(12) 0.0322(3) Uani 1 1 d . A .
O31 O 0.32537(16) 0.39218(5) 0.57177(9) 0.0407(2) Uani 1 1 d . . .
H31 H 0.449(3) 0.4189(8) 0.6099(16) 0.049 Uiso 1 1 d . . .
O32 O 0.53534(16) 0.38380(6) 0.42612(11) 0.0518(3) Uani 1 1 d . . .
C32A C 0.2485(2) 0.29989(7) 0.28315(12) 0.0356(3) Uani 0.313(3) 1 d P A 1
F32 F 0.4136(4) 0.30858(15) 0.2271(3) 0.0480(9) Uani 0.313(3) 1 d P A 1
C32B C 0.2485(2) 0.29989(7) 0.28315(12) 0.0356(3) Uani 0.687(3) 1 d P A 2
H32 H 0.3747 0.3110 0.2513 0.043 Uiso 0.687(3) 1 calc PR A 2
C33 C 0.1044(2) 0.25942(7) 0.21454(13) 0.0404(3) Uani 1 1 d . . .
H33 H 0.1318 0.2430 0.1368 0.049 Uiso 1 1 calc R A 1
C34 C -0.0793(2) 0.24295(7) 0.25960(13) 0.0396(3) Uani 1 1 d . A .
H34 H -0.1792 0.2152 0.2129 0.048 Uiso 1 1 calc R . .
C35 C -0.1175(2) 0.26681(7) 0.37260(13) 0.0369(3) Uani 1 1 d . . .
H35 H -0.2442 0.2557 0.4038 0.044 Uiso 1 1 calc R A 1
C36A C 0.02884(19) 0.30697(6) 0.44059(12) 0.0314(3) Uani 0.313(3) 1 d P A 1
H36 H 0.0015 0.3226 0.5189 0.038 Uiso 0.313(3) 1 calc PR A 1
C36B C 0.02884(19) 0.30697(6) 0.44059(12) 0.0314(3) Uani 0.687(3) 1 d P A 2
F36 F -0.01782(18) 0.32647(6) 0.55198(11) 0.0420(4) Uani 0.687(3) 1 d P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 N12 1.3506(14) . ?
N11 C15 1.3696(15) . ?
N11 C23 1.3996(16) . ?
N12 N13 1.3226(16) . ?
N13 C14 1.3396(17) . ?
C14 C15 1.3807(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.4231(18) . ?
C16 C17 1.349(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.4339(18) . ?
C17 H17 0.9500 . ?
C18 C23 1.4074(16) . ?
C18 C19 1.4083(19) . ?
C19 C20 1.372(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.395(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.3795(19) . ?
C21 H21 0.9500 . ?
C22 C23 1.3881(17) . ?
C22 H22 0.9500 . ?
C31 C36A 1.3870(17) . ?
C31 C32A 1.3931(18) . ?
C31 C37 1.4968(18) . ?
C37 O32 1.2060(16) . ?
C37 O31 1.3189(17) . ?
O31 H31 1.006(18) . ?
C32A F32 1.304(3) . ?
C32A C33 1.381(2) . ?
C33 C34 1.378(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.3774(19) . ?
C34 H34 0.9500 . ?
C35 C36A 1.3830(18) . ?
C35 H35 0.9500 . ?
C36A H36 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N12 N11 C15 111.53(10) . . ?
N12 N11 C23 124.07(10) . . ?
C15 N11 C23 124.40(10) . . ?
N13 N12 N11 105.59(10) . . ?
N12 N13 C14 110.76(11) . . ?
N13 C14 C15 108.56(11) . . ?
N13 C14 H14 125.7 . . ?
C15 C14 H14 125.7 . . ?
N11 C15 C14 103.57(11) . . ?
N11 C15 C16 118.57(12) . . ?
C14 C15 C16 137.86(12) . . ?
C17 C16 C15 119.24(12) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 121.83(11) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C23 C18 C19 117.24(12) . . ?
C23 C18 C17 119.65(12) . . ?
C19 C18 C17 123.11(11) . . ?
C20 C19 C18 121.12(12) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C21 119.99(13) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 120.93(13) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C23 118.67(12) . . ?
C21 C22 H22 120.7 . . ?
C23 C22 H22 120.7 . . ?
C22 C23 N11 121.65(10) . . ?
C22 C23 C18 122.04(12) . . ?
N11 C23 C18 116.30(11) . . ?
C36A C31 C32A 116.82(12) . . ?
C36A C31 C37 123.80(12) . . ?
C32A C31 C37 119.38(11) . . ?
O32 C37 O31 123.40(13) . . ?
O32 C37 C31 121.87(12) . . ?
O31 C37 C31 114.73(11) . . ?
C37 O31 H31 106.2(10) . . ?
F32 C32A C33 110.66(17) . . ?
F32 C32A C31 127.28(17) . . ?
C33 C32A C31 122.03(12) . . ?
C34 C33 C32A 119.61(13) . . ?
C34 C33 H33 120.2 . . ?
C32A C33 H33 120.2 . . ?
C35 C34 C33 119.81(13) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C36A 119.92(13) . . ?
C34 C35 H35 120.0 . . ?
C36A C35 H35 120.0 . . ?
C35 C36A C31 121.81(12) . . ?
C35 C36A H36 119.1 . . ?
C31 C36A H36 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 N12 N13 0.04(13) . . . . ?
C23 N11 N12 N13 -179.27(10) . . . . ?
N11 N12 N13 C14 0.06(14) . . . . ?
N12 N13 C14 C15 -0.13(16) . . . . ?
N12 N11 C15 C14 -0.12(13) . . . . ?
C23 N11 C15 C14 179.19(11) . . . . ?
N12 N11 C15 C16 179.85(11) . . . . ?
C23 N11 C15 C16 -0.84(18) . . . . ?
N13 C14 C15 N11 0.15(14) . . . . ?
N13 C14 C15 C16 -179.81(15) . . . . ?
N11 C15 C16 C17 0.29(18) . . . . ?
C14 C15 C16 C17 -179.75(15) . . . . ?
C15 C16 C17 C18 0.66(19) . . . . ?
C16 C17 C18 C23 -1.11(18) . . . . ?
C16 C17 C18 C19 178.40(12) . . . . ?
C23 C18 C19 C20 0.59(18) . . . . ?
C17 C18 C19 C20 -178.93(12) . . . . ?
C18 C19 C20 C21 -0.6(2) . . . . ?
C19 C20 C21 C22 -0.1(2) . . . . ?
C20 C21 C22 C23 0.70(19) . . . . ?
C21 C22 C23 N11 178.28(11) . . . . ?
C21 C22 C23 C18 -0.67(18) . . . . ?
N12 N11 C23 C22 0.61(17) . . . . ?
C15 N11 C23 C22 -178.62(11) . . . . ?
N12 N11 C23 C18 179.61(10) . . . . ?
C15 N11 C23 C18 0.39(16) . . . . ?
C19 C18 C23 C22 0.04(17) . . . . ?
C17 C18 C23 C22 179.57(11) . . . . ?
C19 C18 C23 N11 -178.97(10) . . . . ?
C17 C18 C23 N11 0.57(16) . . . . ?
C36A C31 C37 O32 179.46(13) . . . . ?
C32A C31 C37 O32 -1.18(19) . . . . ?
C36A C31 C37 O31 -1.19(18) . . . . ?
C32A C31 C37 O31 178.17(11) . . . . ?
C36A C31 C32A F32 -177.7(2) . . . . ?
C37 C31 C32A F32 2.9(3) . . . . ?
C36A C31 C32A C33 0.56(19) . . . . ?
C37 C31 C32A C33 -178.83(12) . . . . ?
F32 C32A C33 C34 178.47(19) . . . . ?
C31 C32A C33 C34 0.0(2) . . . . ?
C32A C33 C34 C35 -0.1(2) . . . . ?
C33 C34 C35 C36A -0.3(2) . . . . ?
C34 C35 C36A C31 0.8(2) . . . . ?
C32A C31 C36A C35 -0.97(19) . . . . ?
C37 C31 C36A C35 178.40(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O31 H31 N13 1.006(18) 1.652(18) 2.6544(15) 173.2(16) .

_diffrn_measured_fraction_theta_max 0.889
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.050
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_A1HB2
_database_code_depnum_ccdc_archive 'CCDC 1505717'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2016-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Mp-p1b-H15 {[1,2,3]Triazolo[1,5-a]quinoline}2, HOOC-(CH2)3-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C10 H7 N3)2 (C5 H8 O4)
;
_chemical_formula_sum            'C25 H22 N6 O4'
_chemical_formula_weight         470.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Fdd2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   28.065(11)
_cell_length_b                   36.966(14)
_cell_length_c                   4.2708(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4431(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1372
_cell_measurement_theta_min      5.81
_cell_measurement_theta_max      25.53

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1968
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9633
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5500
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_sigmaI/netI    0.0853
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_k_max       54
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         5.81
_diffrn_reflns_theta_max         31.67
_reflns_number_total             2425
_reflns_number_gt                1620
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2425
_refine_ls_number_parameters     162
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1260
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.28637(6) 0.57263(5) 0.2291(5) 0.0238(5) Uani 1 1 d . . .
N12 N 0.30564(6) 0.54095(5) 0.3190(6) 0.0285(5) Uani 1 1 d . . .
N13 N 0.34295(7) 0.54945(5) 0.4917(6) 0.0316(5) Uani 1 1 d . . .
C14 C 0.34784(8) 0.58572(7) 0.5097(8) 0.0329(6) Uani 1 1 d . . .
H14 H 0.3722 0.5982 0.6203 0.040 Uiso 1 1 calc R . .
C15 C 0.31170(8) 0.60162(7) 0.3415(7) 0.0290(6) Uani 1 1 d . . .
C16 C 0.29571(8) 0.63726(7) 0.2700(7) 0.0320(6) Uani 1 1 d . . .
H16 H 0.3129 0.6578 0.3429 0.038 Uiso 1 1 calc R . .
C17 C 0.25576(8) 0.64145(6) 0.0969(8) 0.0310(6) Uani 1 1 d . . .
H17 H 0.2446 0.6652 0.0529 0.037 Uiso 1 1 calc R . .
C18 C 0.22973(7) 0.61077(6) -0.0226(7) 0.0257(6) Uani 1 1 d . . .
C19 C 0.18854(8) 0.61457(7) -0.2060(7) 0.0315(7) Uani 1 1 d . . .
H19 H 0.1767 0.6380 -0.2534 0.038 Uiso 1 1 calc R . .
C20 C 0.16517(8) 0.58450(7) -0.3176(8) 0.0349(7) Uani 1 1 d . . .
H20 H 0.1372 0.5874 -0.4401 0.042 Uiso 1 1 calc R . .
C21 C 0.18218(8) 0.54982(7) -0.2528(7) 0.0309(6) Uani 1 1 d . . .
H21 H 0.1659 0.5293 -0.3333 0.037 Uiso 1 1 calc R . .
C22 C 0.22232(8) 0.54523(6) -0.0731(7) 0.0279(6) Uani 1 1 d . . .
H22 H 0.2339 0.5217 -0.0283 0.033 Uiso 1 1 calc R . .
C23 C 0.24565(7) 0.57560(6) 0.0420(7) 0.0243(5) Uani 1 1 d . . .
C31 C 0.42950(7) 0.51274(6) 0.9457(7) 0.0254(5) Uani 1 1 d . . .
O31 O 0.39562(5) 0.49826(5) 0.7698(5) 0.0300(5) Uani 1 1 d . . .
H31 H 0.3770(9) 0.5183(8) 0.672(8) 0.036 Uiso 1 1 d . . .
O32 O 0.43565(6) 0.54515(4) 0.9723(5) 0.0341(5) Uani 1 1 d . . .
C32 C 0.45899(7) 0.48479(6) 1.1092(7) 0.0264(6) Uani 1 1 d . . .
H32A H 0.4721 0.4680 0.9507 0.032 Uiso 1 1 calc R . .
H32B H 0.4380 0.4706 1.2497 0.032 Uiso 1 1 calc R . .
C33 C 0.5000 0.5000 1.3006(9) 0.0257(8) Uani 1 2 d S . .
H33 H 0.5123 0.4812 1.4335 0.031 Uiso 1 1 d R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 N12 1.346(3) . ?
N11 C15 1.373(3) . ?
N11 C23 1.399(3) . ?
N12 N13 1.319(3) . ?
N13 C14 1.350(3) . ?
C14 C15 1.375(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.425(4) . ?
C16 C17 1.352(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.442(3) . ?
C17 H17 0.9500 . ?
C18 C23 1.402(3) . ?
C18 C19 1.404(3) . ?
C19 C20 1.376(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.396(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.373(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(3) . ?
C22 H22 0.9500 . ?
C31 O32 1.216(3) . ?
C31 O31 1.325(3) . ?
C31 C32 1.497(3) . ?
O31 H31 1.00(3) . ?
C32 C33 1.519(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C32 1.519(3) 2_665 ?
C33 H33 0.9610 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N12 N11 C15 111.79(19) . . ?
N12 N11 C23 124.04(18) . . ?
C15 N11 C23 124.17(19) . . ?
N13 N12 N11 105.75(18) . . ?
N12 N13 C14 110.4(2) . . ?
N13 C14 C15 108.7(2) . . ?
N13 C14 H14 125.7 . . ?
C15 C14 H14 125.7 . . ?
N11 C15 C14 103.4(2) . . ?
N11 C15 C16 118.9(2) . . ?
C14 C15 C16 137.7(2) . . ?
C17 C16 C15 119.0(2) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C18 121.5(2) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C23 C18 C19 117.7(2) . . ?
C23 C18 C17 119.9(2) . . ?
C19 C18 C17 122.4(2) . . ?
C20 C19 C18 120.3(2) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.7(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 119.0(2) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C22 C23 N11 121.6(2) . . ?
C22 C23 C18 122.0(2) . . ?
N11 C23 C18 116.5(2) . . ?
O32 C31 O31 123.6(2) . . ?
O32 C31 C32 123.9(2) . . ?
O31 C31 C32 112.5(2) . . ?
C31 O31 H31 108.2(17) . . ?
C31 C32 C33 114.47(18) . . ?
C31 C32 H32A 108.6 . . ?
C33 C32 H32A 108.6 . . ?
C31 C32 H32B 108.6 . . ?
C33 C32 H32B 108.6 . . ?
H32A C32 H32B 107.6 . . ?
C32 C33 C32 114.9(3) . 2_665 ?
C32 C33 H33 108.8 . . ?
C32 C33 H33 108.3 2_665 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 N12 N13 0.7(3) . . . . ?
C23 N11 N12 N13 -179.7(2) . . . . ?
N11 N12 N13 C14 -0.6(3) . . . . ?
N12 N13 C14 C15 0.3(3) . . . . ?
N12 N11 C15 C14 -0.5(3) . . . . ?
C23 N11 C15 C14 179.9(3) . . . . ?
N12 N11 C15 C16 -179.4(3) . . . . ?
C23 N11 C15 C16 1.0(4) . . . . ?
N13 C14 C15 N11 0.1(3) . . . . ?
N13 C14 C15 C16 178.6(3) . . . . ?
N11 C15 C16 C17 0.8(4) . . . . ?
C14 C15 C16 C17 -177.6(3) . . . . ?
C15 C16 C17 C18 -1.5(4) . . . . ?
C16 C17 C18 C23 0.4(4) . . . . ?
C16 C17 C18 C19 -179.2(3) . . . . ?
C23 C18 C19 C20 -0.2(4) . . . . ?
C17 C18 C19 C20 179.3(3) . . . . ?
C18 C19 C20 C21 -0.5(4) . . . . ?
C19 C20 C21 C22 0.7(4) . . . . ?
C20 C21 C22 C23 -0.1(4) . . . . ?
C21 C22 C23 N11 179.3(2) . . . . ?
C21 C22 C23 C18 -0.7(4) . . . . ?
N12 N11 C23 C22 -1.6(4) . . . . ?
C15 N11 C23 C22 178.0(3) . . . . ?
N12 N11 C23 C18 178.4(2) . . . . ?
C15 N11 C23 C18 -2.1(4) . . . . ?
C19 C18 C23 C22 0.9(4) . . . . ?
C17 C18 C23 C22 -178.7(3) . . . . ?
C19 C18 C23 N11 -179.1(2) . . . . ?
C17 C18 C23 N11 1.3(4) . . . . ?
O32 C31 C32 C33 -3.5(4) . . . . ?
O31 C31 C32 C33 177.0(2) . . . . ?
C31 C32 C33 C32 -71.47(19) . . . 2_665 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O31 H31 N13 1.00(3) 1.68(3) 2.679(3) 175(3) .

_diffrn_measured_fraction_theta_max 0.901
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.056
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_A1D1
_database_code_depnum_ccdc_archive 'CCDC 1505718'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2016-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Mp-p1b-H24 {[1,2,3]Triazolo[1,5-a]quinoline}2, 4-I-F4-PhCOOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C10 H7 N3)2 (C7 H F4 I O2)
;
_chemical_formula_sum            'C27 H15 F4 I N6 O2'
_chemical_formula_weight         658.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   6.6580(8)
_cell_length_b                   9.8155(11)
_cell_length_c                   10.4663(13)
_cell_angle_alpha                65.256(4)
_cell_angle_beta                 79.993(4)
_cell_angle_gamma                84.833(4)
_cell_volume                     611.63(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9872
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      31.75

_exptl_crystal_description       plate
_exptl_crystal_colour            bronze
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324
_exptl_absorpt_coefficient_mu    1.380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5820
_exptl_absorpt_correction_T_max  0.8094
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22351
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         31.85
_reflns_number_total             6827
_reflns_number_gt                6777
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0400P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6827
_refine_ls_number_parameters     324
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0633
_refine_ls_wR_factor_gt          0.0629
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 1.3281(2) 0.2022(2) -0.03885(18) 0.0215(2) Uani 1 1 d D . .
N12 N 1.1344(2) 0.1880(2) 0.0304(2) 0.0307(2) Uani 1 1 d D . .
N13 N 1.1267(3) 0.2582(2) 0.1142(2) 0.0363(3) Uani 1 1 d D . .
C14 C 1.3088(3) 0.3146(3) 0.1005(2) 0.0352(3) Uani 1 1 d D . .
H14 H 1.3400 0.3691 0.1510 0.042 Uiso 1 1 calc R . .
C15 C 1.4442(3) 0.2810(2) 0.0012(2) 0.0268(2) Uani 1 1 d D . .
C16 C 1.6530(3) 0.3059(3) -0.0608(2) 0.0336(3) Uani 1 1 d D . .
H16 H 1.7368 0.3587 -0.0327 0.040 Uiso 1 1 calc R . .
C17 C 1.7300(3) 0.2536(2) -0.1597(2) 0.0321(3) Uani 1 1 d D . .
H17 H 1.8685 0.2715 -0.2026 0.038 Uiso 1 1 calc R . .
C18 C 1.6070(2) 0.1714(2) -0.20162(19) 0.0251(2) Uani 1 1 d D . .
C19 C 1.6855(3) 0.1128(3) -0.3025(2) 0.0358(3) Uani 1 1 d D . .
H19 H 1.8238 0.1291 -0.3463 0.043 Uiso 1 1 calc R . .
C20 C 1.5651(4) 0.0330(3) -0.3378(2) 0.0425(4) Uani 1 1 d D . .
H20 H 1.6204 -0.0063 -0.4057 0.051 Uiso 1 1 calc R . .
C21 C 1.3615(4) 0.0084(3) -0.2754(2) 0.0405(3) Uani 1 1 d D . .
H21 H 1.2793 -0.0463 -0.3025 0.049 Uiso 1 1 calc R . .
C22 C 1.2770(3) 0.0623(2) -0.1746(2) 0.0294(2) Uani 1 1 d D . .
H22 H 1.1388 0.0441 -0.1309 0.035 Uiso 1 1 calc R . .
C23 C 1.4011(2) 0.14382(19) -0.13938(17) 0.0214(2) Uani 1 1 d D . .
N31 N -0.3233(2) 0.7976(2) 1.0369(2) 0.0215(2) Uani 1 1 d D . .
N32 N -0.1304(2) 0.8115(3) 0.9662(2) 0.0307(2) Uani 1 1 d D . .
N33 N -0.1250(3) 0.7402(2) 0.8833(2) 0.0363(3) Uani 1 1 d D . .
C34 C -0.3076(3) 0.6833(3) 0.8995(2) 0.0352(3) Uani 1 1 d D . .
H34 H -0.3401 0.6273 0.8507 0.042 Uiso 1 1 calc R . .
C35 C -0.4413(3) 0.7187(2) 0.9982(2) 0.0268(2) Uani 1 1 d D . .
C36 C -0.6496(3) 0.6946(3) 1.0612(2) 0.0336(3) Uani 1 1 d D . .
H36 H -0.7344 0.6413 1.0343 0.040 Uiso 1 1 calc R . .
C37 C -0.7249(3) 0.7483(2) 1.1592(2) 0.0321(3) Uani 1 1 d D . .
H37 H -0.8636 0.7315 1.2021 0.038 Uiso 1 1 calc R . .
C38 C -0.6008(3) 0.8300(2) 1.2003(2) 0.0251(2) Uani 1 1 d D . .
C39 C -0.6775(3) 0.8887(3) 1.3012(2) 0.0358(3) Uani 1 1 d D . .
H39 H -0.8160 0.8735 1.3448 0.043 Uiso 1 1 calc R . .
C40 C -0.5553(4) 0.9670(3) 1.3369(2) 0.0425(4) Uani 1 1 d D . .
H40 H -0.6093 1.0059 1.4054 0.051 Uiso 1 1 calc R . .
C41 C -0.3517(4) 0.9906(3) 1.2741(2) 0.0405(3) Uani 1 1 d D . .
H41 H -0.2685 1.0452 1.3005 0.049 Uiso 1 1 calc R . .
C42 C -0.2689(3) 0.9356(2) 1.1738(2) 0.0294(2) Uani 1 1 d D . .
H42 H -0.1303 0.9521 1.1307 0.035 Uiso 1 1 calc R . .
C43 C -0.3945(2) 0.8557(2) 1.13817(18) 0.0214(2) Uani 1 1 d D . .
I1 I 0.16578(4) 0.61497(4) 0.72265(4) 0.02184(5) Uani 0.6783(4) 1 d PD A 1
C51A C 0.6641(9) 0.4638(12) 0.3974(13) 0.0184(7) Uani 0.6783(4) 1 d PD A 1
C52A C 0.7119(6) 0.5562(7) 0.4582(7) 0.0177(7) Uani 0.6783(4) 1 d PD A 1
C53A C 0.5735(6) 0.5968(8) 0.5505(8) 0.0171(7) Uani 0.6783(4) 1 d PD A 1
C54A C 0.3768(9) 0.5444(11) 0.5904(10) 0.0173(6) Uani 0.6783(4) 1 d PD A 1
C55A C 0.3271(6) 0.4430(10) 0.5407(9) 0.0180(7) Uani 0.6783(4) 1 d PD A 1
C56A C 0.4666(9) 0.4073(15) 0.4444(14) 0.0191(6) Uani 0.6783(4) 1 d PD A 1
F52A F 0.8979(5) 0.6195(10) 0.4191(9) 0.0251(5) Uani 0.6783(4) 1 d PD A 1
F53A F 0.6317(8) 0.6910(12) 0.5975(11) 0.0256(6) Uani 0.6783(4) 1 d PD A 1
F55A F 0.1396(8) 0.3886(10) 0.5754(10) 0.0249(5) Uani 0.6783(4) 1 d PD A 1
F56A F 0.4036(11) 0.3155(16) 0.3934(16) 0.0265(6) Uani 0.6783(4) 1 d PD A 1
C57A C 0.8193(5) 0.4256(4) 0.2937(3) 0.02184(5) Uani 0.6783(4) 1 d PD A 1
O51A O 0.8043(4) 0.2928(3) 0.2986(3) 0.0428(5) Uani 0.6783(4) 1 d PD A 1
H51A H 0.9013 0.2771 0.2430 0.051 Uiso 0.6783(4) 1 calc PR A 1
O52A O 0.9449(5) 0.5169(3) 0.2105(3) 0.0432(5) Uani 0.6783(4) 1 d PD A 1
I2 I 0.84261(7) 0.38537(6) 0.27544(5) 0.02184(5) Uani 0.3217(4) 1 d PD A 2
C51B C 0.3388(18) 0.532(2) 0.600(2) 0.0173(6) Uani 0.3217(4) 1 d PD A 2
C52B C 0.2909(12) 0.442(2) 0.5365(19) 0.0180(7) Uani 0.3217(4) 1 d PD A 2
C53B C 0.4323(17) 0.399(3) 0.447(3) 0.0191(6) Uani 0.3217(4) 1 d PD A 2
C54B C 0.6277(17) 0.453(3) 0.407(3) 0.0184(7) Uani 0.3217(4) 1 d PD A 2
C55B C 0.6718(11) 0.5617(15) 0.4508(15) 0.0177(7) Uani 0.3217(4) 1 d PD A 2
C56B C 0.5311(12) 0.5965(18) 0.5472(17) 0.0171(7) Uani 0.3217(4) 1 d PD A 2
F52B F 0.1092(17) 0.372(2) 0.581(2) 0.0249(5) Uani 0.3217(4) 1 d PD A 2
F53B F 0.377(2) 0.302(4) 0.402(4) 0.0265(6) Uani 0.3217(4) 1 d PD A 2
F55B F 0.8604(13) 0.614(2) 0.420(2) 0.0251(5) Uani 0.3217(4) 1 d PD A 2
F56B F 0.5950(19) 0.685(3) 0.602(2) 0.0256(6) Uani 0.3217(4) 1 d PD A 2
C57B C 0.1826(8) 0.5667(9) 0.7052(7) 0.02184(5) Uani 0.3217(4) 1 d PD A 2
O51B O 0.1995(10) 0.7068(8) 0.6957(7) 0.0428(5) Uani 0.3217(4) 1 d P A 2
H51B H 0.1039 0.7242 0.7511 0.051 Uiso 0.3217(4) 1 calc PR A 2
O52B O 0.0625(10) 0.4831(7) 0.7862(7) 0.0432(5) Uani 0.3217(4) 1 d P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 N12 1.3528(17) . ?
N11 C15 1.3654(18) . ?
N11 C23 1.3962(16) . ?
N12 N13 1.3152(19) . ?
N13 C14 1.338(2) . ?
C14 C15 1.382(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.424(2) . ?
C16 C17 1.345(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.433(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.4077(19) . ?
C18 C23 1.4090(19) . ?
C19 C20 1.361(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.394(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.385(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(2) . ?
C22 H22 0.9500 . ?
N31 N32 1.3540(18) . ?
N31 C35 1.3655(19) . ?
N31 C43 1.3979(17) . ?
N32 N33 1.317(2) . ?
N33 C34 1.338(2) . ?
C34 C35 1.381(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.423(2) . ?
C36 C37 1.345(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.429(2) . ?
C37 H37 0.9500 . ?
C38 C39 1.406(2) . ?
C38 C43 1.4099(19) . ?
C39 C40 1.361(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.394(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.384(2) . ?
C41 H41 0.9500 . ?
C42 C43 1.388(2) . ?
C42 H42 0.9500 . ?
I1 C54A 2.079(5) . ?
C51A C52A 1.390(6) . ?
C51A C56A 1.399(6) . ?
C51A C57A 1.506(5) . ?
C52A F52A 1.355(5) . ?
C52A C53A 1.374(6) . ?
C53A F53A 1.327(5) . ?
C53A C54A 1.380(6) . ?
C54A C55A 1.387(6) . ?
C55A F55A 1.333(4) . ?
C55A C56A 1.383(6) . ?
C56A F56A 1.349(5) . ?
C57A O52A 1.220(4) . ?
C57A O51A 1.295(4) . ?
O51A H51A 0.8400 . ?
I2 C54B 2.078(5) . ?
C51B C52B 1.391(7) . ?
C51B C56B 1.398(6) . ?
C51B C57B 1.506(6) . ?
C52B F52B 1.355(5) . ?
C52B C53B 1.375(6) . ?
C53B F53B 1.327(5) . ?
C53B C54B 1.379(6) . ?
C54B C55B 1.389(6) . ?
C55B F55B 1.333(5) . ?
C55B C56B 1.384(6) . ?
C56B F56B 1.349(6) . ?
C57B O52B 1.154(8) . ?
C57B O51B 1.350(10) . ?
O51B H51B 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N12 N11 C15 111.83(12) . . ?
N12 N11 C23 124.34(13) . . ?
C15 N11 C23 123.83(13) . . ?
N13 N12 N11 105.71(14) . . ?
N12 N13 C14 110.42(14) . . ?
N13 C14 C15 109.12(15) . . ?
N13 C14 H14 125.4 . . ?
C15 C14 H14 125.4 . . ?
N11 C15 C14 102.92(14) . . ?
N11 C15 C16 119.33(14) . . ?
C14 C15 C16 137.75(16) . . ?
C17 C16 C15 119.09(16) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C18 121.28(15) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C19 C18 C23 117.51(15) . . ?
C19 C18 C17 122.25(16) . . ?
C23 C18 C17 120.23(14) . . ?
C20 C19 C18 120.62(17) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 120.66(16) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 121.11(17) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C23 117.79(17) . . ?
C21 C22 H22 121.1 . . ?
C23 C22 H22 121.1 . . ?
C22 C23 N11 121.47(14) . . ?
C22 C23 C18 122.30(14) . . ?
N11 C23 C18 116.22(13) . . ?
N32 N31 C35 111.76(14) . . ?
N32 N31 C43 124.62(14) . . ?
C35 N31 C43 123.63(15) . . ?
N33 N32 N31 105.70(15) . . ?
N32 N33 C34 110.38(15) . . ?
N33 C34 C35 109.17(15) . . ?
N33 C34 H34 125.4 . . ?
C35 C34 H34 125.4 . . ?
N31 C35 C34 103.00(15) . . ?
N31 C35 C36 119.40(15) . . ?
C34 C35 C36 137.60(16) . . ?
C37 C36 C35 119.09(16) . . ?
C37 C36 H36 120.5 . . ?
C35 C36 H36 120.5 . . ?
C36 C37 C38 121.42(16) . . ?
C36 C37 H37 119.3 . . ?
C38 C37 H37 119.3 . . ?
C39 C38 C43 117.62(15) . . ?
C39 C38 C37 122.23(16) . . ?
C43 C38 C37 120.15(14) . . ?
C40 C39 C38 120.65(18) . . ?
C40 C39 H39 119.7 . . ?
C38 C39 H39 119.7 . . ?
C39 C40 C41 120.60(17) . . ?
C39 C40 H40 119.7 . . ?
C41 C40 H40 119.7 . . ?
C42 C41 C40 121.04(17) . . ?
C42 C41 H41 119.5 . . ?
C40 C41 H41 119.5 . . ?
C41 C42 C43 117.97(17) . . ?
C41 C42 H42 121.0 . . ?
C43 C42 H42 121.0 . . ?
C42 C43 N31 121.57(14) . . ?
C42 C43 C38 122.12(14) . . ?
N31 C43 C38 116.31(14) . . ?
C52A C51A C56A 114.7(4) . . ?
C52A C51A C57A 121.2(4) . . ?
C56A C51A C57A 124.1(4) . . ?
F52A C52A C53A 116.8(4) . . ?
F52A C52A C51A 119.9(4) . . ?
C53A C52A C51A 123.1(4) . . ?
F53A C53A C52A 118.3(4) . . ?
F53A C53A C54A 120.6(4) . . ?
C52A C53A C54A 121.0(4) . . ?
C53A C54A C55A 117.8(4) . . ?
C53A C54A I1 120.4(3) . . ?
C55A C54A I1 121.8(3) . . ?
F55A C55A C56A 119.1(4) . . ?
F55A C55A C54A 120.6(4) . . ?
C56A C55A C54A 120.1(4) . . ?
F56A C56A C55A 117.0(4) . . ?
F56A C56A C51A 119.9(4) . . ?
C55A C56A C51A 123.1(4) . . ?
O52A C57A O51A 124.0(3) . . ?
O52A C57A C51A 120.9(4) . . ?
O51A C57A C51A 115.0(4) . . ?
C57A O51A H51A 109.5 . . ?
C52B C51B C56B 114.7(5) . . ?
C52B C51B C57B 120.8(5) . . ?
C56B C51B C57B 124.2(5) . . ?
F52B C52B C53B 116.6(5) . . ?
F52B C52B C51B 119.8(6) . . ?
C53B C52B C51B 122.7(5) . . ?
F53B C53B C52B 118.1(5) . . ?
F53B C53B C54B 121.1(5) . . ?
C52B C53B C54B 120.8(5) . . ?
C53B C54B C55B 117.9(5) . . ?
C53B C54B I2 120.7(4) . . ?
C55B C54B I2 121.3(4) . . ?
F55B C55B C56B 118.9(5) . . ?
F55B C55B C54B 120.2(5) . . ?
C56B C55B C54B 119.9(5) . . ?
F56B C56B C55B 116.8(5) . . ?
F56B C56B C51B 120.0(5) . . ?
C55B C56B C51B 122.8(5) . . ?
O52B C57B O51B 123.4(5) . . ?
O52B C57B C51B 124.1(8) . . ?
O51B C57B C51B 112.6(8) . . ?
C57B O51B H51B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 N12 N13 0.3(3) . . . . ?
C23 N11 N12 N13 -179.7(2) . . . . ?
N11 N12 N13 C14 -0.5(3) . . . . ?
N12 N13 C14 C15 0.6(3) . . . . ?
N12 N11 C15 C14 0.1(2) . . . . ?
C23 N11 C15 C14 180.0(2) . . . . ?
N12 N11 C15 C16 179.6(2) . . . . ?
C23 N11 C15 C16 -0.5(3) . . . . ?
N13 C14 C15 N11 -0.4(3) . . . . ?
N13 C14 C15 C16 -179.8(3) . . . . ?
N11 C15 C16 C17 1.3(3) . . . . ?
C14 C15 C16 C17 -179.3(3) . . . . ?
C15 C16 C17 C18 -1.1(3) . . . . ?
C16 C17 C18 C19 -178.5(2) . . . . ?
C16 C17 C18 C23 0.0(3) . . . . ?
C23 C18 C19 C20 0.2(3) . . . . ?
C17 C18 C19 C20 178.8(2) . . . . ?
C18 C19 C20 C21 0.3(4) . . . . ?
C19 C20 C21 C22 -1.0(4) . . . . ?
C20 C21 C22 C23 1.0(3) . . . . ?
C21 C22 C23 N11 180.0(2) . . . . ?
C21 C22 C23 C18 -0.5(3) . . . . ?
N12 N11 C23 C22 -1.1(3) . . . . ?
C15 N11 C23 C22 178.9(2) . . . . ?
N12 N11 C23 C18 179.30(19) . . . . ?
C15 N11 C23 C18 -0.6(3) . . . . ?
C19 C18 C23 C22 -0.1(3) . . . . ?
C17 C18 C23 C22 -178.7(2) . . . . ?
C19 C18 C23 N11 179.46(19) . . . . ?
C17 C18 C23 N11 0.8(3) . . . . ?
C35 N31 N32 N33 -0.5(3) . . . . ?
C43 N31 N32 N33 179.1(2) . . . . ?
N31 N32 N33 C34 0.3(3) . . . . ?
N32 N33 C34 C35 0.1(3) . . . . ?
N32 N31 C35 C34 0.5(3) . . . . ?
C43 N31 C35 C34 -179.1(2) . . . . ?
N32 N31 C35 C36 -179.4(2) . . . . ?
C43 N31 C35 C36 1.0(4) . . . . ?
N33 C34 C35 N31 -0.4(3) . . . . ?
N33 C34 C35 C36 179.5(3) . . . . ?
N31 C35 C36 C37 -1.0(3) . . . . ?
C34 C35 C36 C37 179.1(3) . . . . ?
C35 C36 C37 C38 0.6(3) . . . . ?
C36 C37 C38 C39 179.1(2) . . . . ?
C36 C37 C38 C43 -0.2(3) . . . . ?
C43 C38 C39 C40 -0.2(3) . . . . ?
C37 C38 C39 C40 -179.5(2) . . . . ?
C38 C39 C40 C41 0.1(4) . . . . ?
C39 C40 C41 C42 0.2(4) . . . . ?
C40 C41 C42 C43 -0.3(3) . . . . ?
C41 C42 C43 N31 179.4(2) . . . . ?
C41 C42 C43 C38 0.2(3) . . . . ?
N32 N31 C43 C42 0.6(4) . . . . ?
C35 N31 C43 C42 -179.8(2) . . . . ?
N32 N31 C43 C38 179.9(2) . . . . ?
C35 N31 C43 C38 -0.6(3) . . . . ?
C39 C38 C43 C42 0.0(3) . . . . ?
C37 C38 C43 C42 179.4(2) . . . . ?
C39 C38 C43 N31 -179.2(2) . . . . ?
C37 C38 C43 N31 0.1(3) . . . . ?
C56A C51A C52A F52A -178.9(10) . . . . ?
C57A C51A C52A F52A 3.2(14) . . . . ?
C56A C51A C52A C53A -3.8(14) . . . . ?
C57A C51A C52A C53A 178.3(8) . . . . ?
F52A C52A C53A F53A -1.7(11) . . . . ?
C51A C52A C53A F53A -176.9(10) . . . . ?
F52A C52A C53A C54A 176.5(8) . . . . ?
C51A C52A C53A C54A 1.3(11) . . . . ?
F53A C53A C54A C55A -178.3(10) . . . . ?
C52A C53A C54A C55A 3.5(13) . . . . ?
F53A C53A C54A I1 1.0(13) . . . . ?
C52A C53A C54A I1 -177.1(6) . . . . ?
C53A C54A C55A F55A -179.9(9) . . . . ?
I1 C54A C55A F55A 0.8(13) . . . . ?
C53A C54A C55A C56A -5.6(14) . . . . ?
I1 C54A C55A C56A 175.1(9) . . . . ?
F55A C55A C56A F56A -1.4(18) . . . . ?
C54A C55A C56A F56A -175.8(13) . . . . ?
F55A C55A C56A C51A 177.4(13) . . . . ?
C54A C55A C56A C51A 3.0(18) . . . . ?
C52A C51A C56A F56A -179.6(14) . . . . ?
C57A C51A C56A F56A -2(2) . . . . ?
C52A C51A C56A C55A 1.7(19) . . . . ?
C57A C51A C56A C55A 179.4(11) . . . . ?
C52A C51A C57A O52A -34.8(14) . . . . ?
C56A C51A C57A O52A 147.6(11) . . . . ?
C52A C51A C57A O51A 146.8(8) . . . . ?
C56A C51A C57A O51A -30.9(15) . . . . ?
C56B C51B C52B F52B 179(2) . . . . ?
C57B C51B C52B F52B -7(3) . . . . ?
C56B C51B C52B C53B 11(3) . . . . ?
C57B C51B C52B C53B -176(2) . . . . ?
F52B C52B C53B F53B 5(4) . . . . ?
C51B C52B C53B F53B 174(3) . . . . ?
F52B C52B C53B C54B -174(3) . . . . ?
C51B C52B C53B C54B -5(4) . . . . ?
F53B C53B C54B C55B 176(3) . . . . ?
C52B C53B C54B C55B -5(4) . . . . ?
F53B C53B C54B I2 0(5) . . . . ?
C52B C53B C54B I2 179(2) . . . . ?
C53B C54B C55B F55B 178(3) . . . . ?
I2 C54B C55B F55B -7(3) . . . . ?
C53B C54B C55B C56B 9(3) . . . . ?
I2 C54B C55B C56B -175.1(17) . . . . ?
F55B C55B C56B F56B 1(3) . . . . ?
C54B C55B C56B F56B 170(2) . . . . ?
F55B C55B C56B C51B -172(2) . . . . ?
C54B C55B C56B C51B -3(3) . . . . ?
C52B C51B C56B F56B -179(2) . . . . ?
C57B C51B C56B F56B 7(3) . . . . ?
C52B C51B C56B C55B -7(3) . . . . ?
C57B C51B C56B C55B 179.8(18) . . . . ?
C52B C51B C57B O52B 36(3) . . . . ?
C56B C51B C57B O52B -150.8(18) . . . . ?
C52B C51B C57B O51B -144.7(18) . . . . ?
C56B C51B C57B O51B 29(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O51A H51A N13 0.84 1.89 2.725(3) 175.1 .
O51B H51B N33 0.84 1.92 2.751(6) 173.1 .

_diffrn_measured_fraction_theta_max 0.907
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.764
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.063
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_A2XB3
_database_code_depnum_ccdc_archive 'CCDC 1505719'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2016-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Mp-p1b-H29 [1,2,3]Triazolo[1,5-a]pyridine, 1,3,5-F3-2,4,6-I3-benzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C6 H5 N3) (C6 F3 I3)
;
_chemical_formula_sum            'C12 H5 F3 I3 N3'
_chemical_formula_weight         628.89

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.3698(6)
_cell_length_b                   13.7351(9)
_cell_length_c                   12.2408(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.6496(15)
_cell_angle_gamma                90.00
_cell_volume                     1575.23(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      31.97

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    5.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1984
_exptl_absorpt_correction_T_max  0.2506
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16602
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         32.07
_reflns_number_total             4882
_reflns_number_gt                4468
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0200P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4882
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0598
_refine_ls_wR_factor_gt          0.0585
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_restrained_S_all      1.210
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.7063(3) 0.4510(2) 0.5158(2) 0.0161(5) Uani 1 1 d . . .
N12 N 0.6027(3) 0.3918(2) 0.4775(2) 0.0197(6) Uani 1 1 d . . .
N13 N 0.6098(3) 0.3122(2) 0.5387(2) 0.0194(6) Uani 1 1 d . . .
C14 C 0.7144(4) 0.3200(3) 0.6130(3) 0.0182(6) Uani 1 1 d . . .
H14 H 0.7396 0.2719 0.6656 0.022 Uiso 1 1 calc R . .
C15 C 0.7800(3) 0.4092(3) 0.6012(3) 0.0164(6) Uani 1 1 d . . .
C16 C 0.8907(4) 0.4629(3) 0.6519(3) 0.0305(9) Uani 1 1 d . . .
H16 H 0.9450 0.4356 0.7103 0.037 Uiso 1 1 calc R . .
C17 C 0.9177(4) 0.5531(3) 0.6161(4) 0.0408(11) Uani 1 1 d . . .
H17 H 0.9918 0.5901 0.6497 0.049 Uiso 1 1 calc R . .
C18 C 0.8373(5) 0.5942(3) 0.5287(4) 0.0396(11) Uani 1 1 d . . .
H18 H 0.8576 0.6586 0.5053 0.047 Uiso 1 1 calc R . .
C19 C 0.7324(4) 0.5435(3) 0.4782(3) 0.0274(8) Uani 1 1 d . . .
H19 H 0.6789 0.5706 0.4192 0.033 Uiso 1 1 calc R . .
C21 C 0.2733(3) 0.0365(2) 0.5128(2) 0.0126(6) Uani 1 1 d . . .
I1 I 0.41127(2) 0.155983(14) 0.524210(16) 0.01425(5) Uani 1 1 d . . .
C22 C 0.1958(3) 0.0192(2) 0.4175(2) 0.0134(6) Uani 1 1 d . . .
F22 F 0.2013(2) 0.08568(14) 0.33780(15) 0.0205(4) Uani 1 1 d . . .
C23 C 0.1134(3) -0.0635(2) 0.4006(2) 0.0125(6) Uani 1 1 d . . .
I2 I 0.01770(2) -0.090464(16) 0.249081(16) 0.01673(6) Uani 1 1 d . . .
C24 C 0.1047(3) -0.1277(2) 0.4872(3) 0.0138(6) Uani 1 1 d . . .
F24 F 0.0223(2) -0.20687(14) 0.47562(16) 0.0203(4) Uani 1 1 d . . .
C25 C 0.1773(3) -0.1141(2) 0.5851(2) 0.0128(6) Uani 1 1 d . . .
I3 I 0.16236(3) -0.212620(16) 0.712892(17) 0.02079(6) Uani 1 1 d . . .
C26 C 0.2614(3) -0.0319(2) 0.5947(2) 0.0128(6) Uani 1 1 d . . .
F26 F 0.3356(2) -0.01753(15) 0.68798(15) 0.0182(4) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 N12 1.347(4) . ?
N11 C15 1.372(4) . ?
N11 C19 1.374(5) . ?
N12 N13 1.326(4) . ?
N13 C14 1.334(4) . ?
N13 I1 2.845(3) . ?
C14 C15 1.379(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.411(5) . ?
C16 C17 1.340(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.419(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.348(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C21 C26 1.380(4) . ?
C21 C22 1.387(4) . ?
C21 I1 2.093(3) . ?
C22 F22 1.338(3) . ?
C22 C23 1.387(4) . ?
C23 C24 1.381(4) . ?
C23 I2 2.085(3) . ?
I2 N12 2.992(3) 2_545 ?
C24 F24 1.341(4) . ?
C24 C25 1.384(4) . ?
C25 C26 1.381(4) . ?
C25 I3 2.075(3) . ?
C26 F26 1.345(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N12 N11 C15 111.5(3) . . ?
N12 N11 C19 124.9(3) . . ?
C15 N11 C19 123.5(3) . . ?
N13 N12 N11 105.6(3) . . ?
N12 N13 C14 110.6(3) . . ?
N12 N13 I1 123.9(2) . . ?
C14 N13 I1 125.3(2) . . ?
N13 C14 C15 108.9(3) . . ?
N13 C14 H14 125.5 . . ?
C15 C14 H14 125.5 . . ?
N11 C15 C14 103.3(3) . . ?
N11 C15 C16 118.5(3) . . ?
C14 C15 C16 138.1(4) . . ?
C17 C16 C15 118.7(4) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 120.9(4) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 121.2(4) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 N11 117.1(4) . . ?
C18 C19 H19 121.4 . . ?
N11 C19 H19 121.4 . . ?
C26 C21 C22 116.6(3) . . ?
C26 C21 I1 122.7(2) . . ?
C22 C21 I1 120.5(2) . . ?
C21 I1 N13 177.31(10) . . ?
F22 C22 C23 118.4(3) . . ?
F22 C22 C21 118.2(3) . . ?
C23 C22 C21 123.5(3) . . ?
C24 C23 C22 116.5(3) . . ?
C24 C23 I2 122.7(2) . . ?
C22 C23 I2 120.8(2) . . ?
C23 I2 N12 173.32(11) . 2_545 ?
F24 C24 C23 118.5(3) . . ?
F24 C24 C25 118.5(3) . . ?
C23 C24 C25 123.0(3) . . ?
C26 C25 C24 117.3(3) . . ?
C26 C25 I3 120.8(2) . . ?
C24 C25 I3 121.9(2) . . ?
F26 C26 C21 118.1(3) . . ?
F26 C26 C25 118.8(3) . . ?
C21 C26 C25 123.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 N12 N13 0.1(4) . . . . ?
C19 N11 N12 N13 -177.1(3) . . . . ?
N11 N12 N13 C14 -0.2(4) . . . . ?
N11 N12 N13 I1 174.41(19) . . . . ?
N12 N13 C14 C15 0.2(4) . . . . ?
I1 N13 C14 C15 -174.3(2) . . . . ?
N12 N11 C15 C14 0.0(4) . . . . ?
C19 N11 C15 C14 177.3(3) . . . . ?
N12 N11 C15 C16 -178.8(3) . . . . ?
C19 N11 C15 C16 -1.5(5) . . . . ?
N13 C14 C15 N11 -0.1(4) . . . . ?
N13 C14 C15 C16 178.3(4) . . . . ?
N11 C15 C16 C17 1.3(5) . . . . ?
C14 C15 C16 C17 -177.0(4) . . . . ?
C15 C16 C17 C18 -0.2(6) . . . . ?
C16 C17 C18 C19 -0.8(7) . . . . ?
C17 C18 C19 N11 0.6(6) . . . . ?
N12 N11 C19 C18 177.5(3) . . . . ?
C15 N11 C19 C18 0.6(5) . . . . ?
C26 C21 C22 F22 177.9(3) . . . . ?
I1 C21 C22 F22 -6.4(4) . . . . ?
C26 C21 C22 C23 -2.3(5) . . . . ?
I1 C21 C22 C23 173.5(2) . . . . ?
F22 C22 C23 C24 -176.6(3) . . . . ?
C21 C22 C23 C24 3.5(5) . . . . ?
F22 C22 C23 I2 6.3(4) . . . . ?
C21 C22 C23 I2 -173.6(2) . . . . ?
C22 C23 C24 F24 177.8(3) . . . . ?
I2 C23 C24 F24 -5.2(4) . . . . ?
C22 C23 C24 C25 -2.4(5) . . . . ?
I2 C23 C24 C25 174.6(2) . . . . ?
F24 C24 C25 C26 180.0(3) . . . . ?
C23 C24 C25 C26 0.1(5) . . . . ?
F24 C24 C25 I3 0.2(4) . . . . ?
C23 C24 C25 I3 -179.6(2) . . . . ?
C22 C21 C26 F26 179.7(3) . . . . ?
I1 C21 C26 F26 4.1(4) . . . . ?
C22 C21 C26 C25 -0.2(4) . . . . ?
I1 C21 C26 C25 -175.9(2) . . . . ?
C24 C25 C26 F26 -178.7(3) . . . . ?
I3 C25 C26 F26 1.1(4) . . . . ?
C24 C25 C26 C21 1.2(5) . . . . ?
I3 C25 C26 C21 -179.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.889
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.681
_refine_diff_density_min         -1.055
_refine_diff_density_rms         0.177
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_A2XB2
_database_code_depnum_ccdc_archive 'CCDC 1505720'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2016-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
Mp-p1b-H28 [1,2,3]triazolo[1,5-a]pyridine, 1,2-diiodotetrafluorobenzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C6 H5 N3) (C6 F4 I2)
;
_chemical_formula_sum            'C12 H5 F4 I2 N3'
_chemical_formula_weight         520.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.1237(17)
_cell_length_b                   7.1542(15)
_cell_length_c                   12.318(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.502(7)
_cell_angle_gamma                90
_cell_volume                     715.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9371
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      31.99

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.419
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    4.437
_shelx_estimated_absorpt_T_min   0.298
_shelx_estimated_absorpt_T_max   0.718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.642
_exptl_absorpt_correction_T_max  0.718
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10644
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.510
_diffrn_reflns_theta_max         32.045
_diffrn_reflns_theta_full        30.000
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_point_group_measured_fraction_full 0.948
_reflns_number_total             4292
_reflns_number_gt                4187
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_max     0.772
_reflns_Friedel_fraction_full    0.892

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0250P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1718 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.041(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4292
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0187
_refine_ls_R_factor_gt           0.0180
_refine_ls_wR_factor_ref         0.0502
_refine_ls_wR_factor_gt          0.0499
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.6560(4) 0.8153(5) 0.2501(3) 0.0152(6) Uani 1 1 d . . . . .
N12 N 0.5676(4) 0.6667(5) 0.2826(3) 0.0185(6) Uani 1 1 d . . . . .
N13 N 0.5157(4) 0.5797(5) 0.1921(3) 0.0216(7) Uani 1 1 d . . . . .
C14 C 0.5683(5) 0.6689(6) 0.1042(3) 0.0220(8) Uani 1 1 d . . . . .
H14 H 0.5468 0.6324 0.0308 0.026 Uiso 1 1 calc R U . . .
C15 C 0.6598(5) 0.8241(6) 0.1389(3) 0.0166(7) Uani 1 1 d . . . . .
C16 C 0.7469(5) 0.9731(6) 0.0924(3) 0.0208(8) Uani 1 1 d . . . . .
H16 H 0.7520 0.9840 0.0157 0.025 Uiso 1 1 calc R U . . .
C17 C 0.8229(6) 1.1002(6) 0.1590(4) 0.0230(8) Uani 1 1 d . . . . .
H17 H 0.8813 1.2013 0.1288 0.028 Uiso 1 1 calc R U . . .
C18 C 0.8159(5) 1.0832(6) 0.2744(3) 0.0208(8) Uani 1 1 d . . . . .
H18 H 0.8708 1.1726 0.3200 0.025 Uiso 1 1 calc R U . . .
C19 C 0.7330(5) 0.9427(6) 0.3191(3) 0.0196(7) Uani 1 1 d . . . . .
H19 H 0.7275 0.9315 0.3957 0.024 Uiso 1 1 calc R U . . .
C31 C 0.7722(5) 0.3857(6) 0.6412(3) 0.0167(7) Uani 1 1 d . . . . .
I1 I 0.66806(3) 0.50058(4) 0.49799(2) 0.01801(6) Uani 1 1 d . . . . .
C32 C 0.7580(4) 0.4651(5) 0.7439(3) 0.0153(7) Uani 1 1 d . . . . .
I2 I 0.64362(3) 0.72326(3) 0.77004(2) 0.01639(6) Uani 1 1 d . . . . .
C33 C 0.8264(5) 0.3732(6) 0.8337(3) 0.0176(7) Uani 1 1 d . . . . .
F33 F 0.8130(3) 0.4420(4) 0.93452(19) 0.0254(5) Uani 1 1 d . . . . .
C34 C 0.9128(5) 0.2091(6) 0.8240(3) 0.0193(7) Uani 1 1 d . . . . .
F34 F 0.9818(3) 0.1239(4) 0.9114(2) 0.0272(6) Uani 1 1 d . . . . .
C35 C 0.9302(5) 0.1316(6) 0.7220(3) 0.0194(7) Uani 1 1 d . . . . .
F35 F 1.0167(3) -0.0243(4) 0.7118(2) 0.0292(6) Uani 1 1 d . . . . .
C36 C 0.8575(5) 0.2191(7) 0.6322(3) 0.0191(7) Uani 1 1 d . . . . .
F36 F 0.8744(4) 0.1373(4) 0.5355(2) 0.0275(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 N12 1.354(5) . ?
N11 C15 1.373(5) . ?
N11 C19 1.378(5) . ?
N12 N13 1.329(5) . ?
N12 I1 2.988(3) . ?
N13 C14 1.343(5) . ?
C14 C15 1.393(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.415(5) . ?
C16 C17 1.355(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.430(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.341(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C31 C36 1.385(6) . ?
C31 C32 1.397(5) . ?
C31 I1 2.091(4) . ?
C32 C33 1.382(5) . ?
C32 I2 2.098(4) . ?
I2 N13 2.907(4) 2_656 ?
C33 F33 1.344(5) . ?
C33 C34 1.376(6) . ?
C34 F34 1.339(4) . ?
C34 C35 1.386(6) . ?
C35 F35 1.327(5) . ?
C35 C36 1.381(6) . ?
C36 F36 1.340(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N12 N11 C15 111.5(3) . . ?
N12 N11 C19 124.7(3) . . ?
C15 N11 C19 123.8(3) . . ?
N13 N12 N11 105.8(3) . . ?
N13 N12 I1 128.5(3) . . ?
N11 N12 I1 116.6(2) . . ?
N12 N13 C14 110.7(3) . . ?
N13 C14 C15 108.4(3) . . ?
N13 C14 H14 125.8 . . ?
C15 C14 H14 125.8 . . ?
N11 C15 C14 103.6(3) . . ?
N11 C15 C16 118.1(3) . . ?
C14 C15 C16 138.3(4) . . ?
C17 C16 C15 118.9(4) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 120.5(4) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 121.0(4) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 N11 117.7(4) . . ?
C18 C19 H19 121.2 . . ?
N11 C19 H19 121.2 . . ?
C36 C31 C32 118.9(3) . . ?
C36 C31 I1 117.1(3) . . ?
C32 C31 I1 123.9(3) . . ?
C31 I1 N12 171.93(13) . . ?
C33 C32 C31 119.0(4) . . ?
C33 C32 I2 117.5(3) . . ?
C31 C32 I2 123.5(3) . . ?
C32 I2 N13 179.53(13) . 2_656 ?
F33 C33 C34 117.1(3) . . ?
F33 C33 C32 121.3(4) . . ?
C34 C33 C32 121.7(4) . . ?
F34 C34 C33 121.0(4) . . ?
F34 C34 C35 119.4(4) . . ?
C33 C34 C35 119.6(3) . . ?
F35 C35 C36 121.0(4) . . ?
F35 C35 C34 119.9(4) . . ?
C36 C35 C34 119.2(4) . . ?
F36 C36 C35 117.2(4) . . ?
F36 C36 C31 121.2(3) . . ?
C35 C36 C31 121.6(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 N12 N13 0.4(4) . . . . ?
C19 N11 N12 N13 -179.6(4) . . . . ?
C15 N11 N12 I1 150.3(2) . . . . ?
C19 N11 N12 I1 -29.7(5) . . . . ?
N11 N12 N13 C14 -0.1(5) . . . . ?
I1 N12 N13 C14 -145.2(3) . . . . ?
N12 N13 C14 C15 -0.2(5) . . . . ?
N12 N11 C15 C14 -0.5(4) . . . . ?
C19 N11 C15 C14 179.5(4) . . . . ?
N12 N11 C15 C16 179.6(3) . . . . ?
C19 N11 C15 C16 -0.4(6) . . . . ?
N13 C14 C15 N11 0.4(5) . . . . ?
N13 C14 C15 C16 -179.7(5) . . . . ?
N11 C15 C16 C17 0.2(6) . . . . ?
C14 C15 C16 C17 -179.8(5) . . . . ?
C15 C16 C17 C18 0.3(7) . . . . ?
C16 C17 C18 C19 -0.7(7) . . . . ?
C17 C18 C19 N11 0.4(6) . . . . ?
N12 N11 C19 C18 -179.9(4) . . . . ?
C15 N11 C19 C18 0.1(6) . . . . ?
C36 C31 C32 C33 -1.3(6) . . . . ?
I1 C31 C32 C33 177.5(3) . . . . ?
C36 C31 C32 I2 176.7(3) . . . . ?
I1 C31 C32 I2 -4.5(5) . . . . ?
C31 C32 C33 F33 -178.6(4) . . . . ?
I2 C32 C33 F33 3.3(5) . . . . ?
C31 C32 C33 C34 2.2(6) . . . . ?
I2 C32 C33 C34 -175.9(3) . . . . ?
F33 C33 C34 F34 -0.9(6) . . . . ?
C32 C33 C34 F34 178.4(4) . . . . ?
F33 C33 C34 C35 179.8(4) . . . . ?
C32 C33 C34 C35 -0.9(6) . . . . ?
F34 C34 C35 F35 -1.0(6) . . . . ?
C33 C34 C35 F35 178.4(4) . . . . ?
F34 C34 C35 C36 179.4(4) . . . . ?
C33 C34 C35 C36 -1.2(6) . . . . ?
F35 C35 C36 F36 1.8(6) . . . . ?
C34 C35 C36 F36 -178.6(4) . . . . ?
F35 C35 C36 C31 -177.5(4) . . . . ?
C34 C35 C36 C31 2.1(6) . . . . ?
C32 C31 C36 F36 179.9(4) . . . . ?
I1 C31 C36 F36 1.0(5) . . . . ?
C32 C31 C36 C35 -0.8(6) . . . . ?
I1 C31 C36 C35 -179.7(3) . . . . ?

_refine_diff_density_max         0.898
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.165

